JPS5842199B2 - エストリオ−ルユウドウタイノ セイゾウホウ - Google Patents
エストリオ−ルユウドウタイノ セイゾウホウInfo
- Publication number
- JPS5842199B2 JPS5842199B2 JP50024452A JP2445275A JPS5842199B2 JP S5842199 B2 JPS5842199 B2 JP S5842199B2 JP 50024452 A JP50024452 A JP 50024452A JP 2445275 A JP2445275 A JP 2445275A JP S5842199 B2 JPS5842199 B2 JP S5842199B2
- Authority
- JP
- Japan
- Prior art keywords
- estriol
- oxide
- group
- compound
- chloroform
- 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.)
- Expired
Links
- PROQIPRRNZUXQM-UHFFFAOYSA-N (16alpha,17betaOH)-Estra-1,3,5(10)-triene-3,16,17-triol Natural products OC1=CC=C2C3CCC(C)(C(C(O)C4)O)C4C3CCC2=C1 PROQIPRRNZUXQM-UHFFFAOYSA-N 0.000 claims description 15
- 229960001348 estriol Drugs 0.000 claims description 15
- PROQIPRRNZUXQM-ZXXIGWHRSA-N estriol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H]([C@H](O)C4)O)[C@@H]4[C@@H]3CCC2=C1 PROQIPRRNZUXQM-ZXXIGWHRSA-N 0.000 claims description 15
- -1 oxidonicotinoyloxy Chemical group 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 150000002166 estriols Chemical class 0.000 claims description 3
- 125000001887 cyclopentyloxy group Chemical group C1(CCCC1)O* 0.000 claims description 2
- BOTLEXFFFSMRLQ-UHFFFAOYSA-N cyclopentyloxycyclopentane Chemical compound C1CCCC1OC1CCCC1 BOTLEXFFFSMRLQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- FJCFFCXMEXZEIM-UHFFFAOYSA-N oxiniacic acid Chemical class OC(=O)C1=CC=C[N+]([O-])=C1 FJCFFCXMEXZEIM-UHFFFAOYSA-N 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 16
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- 230000000694 effects Effects 0.000 description 10
- DNXHEGUUPJUMQT-UHFFFAOYSA-N (+)-estrone Natural products OC1=CC=C2C3CCC(C)(C(CC4)=O)C4C3CCC2=C1 DNXHEGUUPJUMQT-UHFFFAOYSA-N 0.000 description 7
- 229940011871 estrogen Drugs 0.000 description 7
- 239000000262 estrogen Substances 0.000 description 7
- 230000000055 hyoplipidemic effect Effects 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 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 4
- 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 description 4
- 208000031226 Hyperlipidaemia Diseases 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- 229960005309 estradiol Drugs 0.000 description 4
- 229930182833 estradiol Natural products 0.000 description 4
- 230000001076 estrogenic effect Effects 0.000 description 4
- 229960003399 estrone Drugs 0.000 description 4
- 150000002632 lipids Chemical class 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 230000001225 therapeutic effect Effects 0.000 description 4
- 238000011282 treatment Methods 0.000 description 4
- 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 3
- 238000000034 method Methods 0.000 description 3
- 229940063238 premarin Drugs 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 3
- 206010021024 Hypolipidaemia Diseases 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- KNHUKKLJHYUCFP-UHFFFAOYSA-N clofibrate Chemical compound CCOC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 KNHUKKLJHYUCFP-UHFFFAOYSA-N 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- UHQGCIIQUZBJAE-QKDSSNGWSA-N 3-Methoxyestriol Chemical compound C1C[C@]2(C)[C@@H](O)[C@H](O)C[C@H]2[C@@H]2CCC3=CC(OC)=CC=C3[C@H]21 UHQGCIIQUZBJAE-QKDSSNGWSA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- 206010003210 Arteriosclerosis Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 206010067572 Oestrogenic effect Diseases 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
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 208000011775 arteriosclerosis disease Diseases 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 229960001214 clofibrate Drugs 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 230000003054 hormonal effect Effects 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 210000004347 intestinal mucosa Anatomy 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 230000003780 keratinization Effects 0.000 description 1
- 230000037356 lipid metabolism Effects 0.000 description 1
- 230000001000 lipidemic effect Effects 0.000 description 1
- 229960003512 nicotinic acid Drugs 0.000 description 1
- PVNIIMVLHYAWGP-UHFFFAOYSA-N nicotinic acid Natural products OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- ATBIAJXSKNPHEI-UHFFFAOYSA-N pyridine-3-carbonyl chloride Chemical compound ClC(=O)C1=CC=CN=C1 ATBIAJXSKNPHEI-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J43/00—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C07J43/003—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton not condensed
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Obesity (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Hematology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB871274A GB1452794A (en) | 1974-02-26 | 1974-02-26 | Estriol derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS50142555A JPS50142555A (en:Method) | 1975-11-17 |
| JPS5842199B2 true JPS5842199B2 (ja) | 1983-09-17 |
Family
ID=9857798
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP50024452A Expired JPS5842199B2 (ja) | 1974-02-26 | 1975-02-26 | エストリオ−ルユウドウタイノ セイゾウホウ |
Country Status (14)
| Country | Link |
|---|---|
| JP (1) | JPS5842199B2 (en:Method) |
| AR (1) | AR206704A1 (en:Method) |
| BE (1) | BE826016A (en:Method) |
| BR (1) | BR7501131A (en:Method) |
| CA (1) | CA1062699A (en:Method) |
| CH (1) | CH614218A5 (en:Method) |
| ES (1) | ES434961A1 (en:Method) |
| FR (1) | FR2261775B1 (en:Method) |
| GB (1) | GB1452794A (en:Method) |
| IE (1) | IE40689B1 (en:Method) |
| IT (1) | IT1048803B (en:Method) |
| LU (1) | LU71909A1 (en:Method) |
| NL (1) | NL180108C (en:Method) |
| SE (1) | SE419091B (en:Method) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60258198A (ja) * | 1984-06-04 | 1985-12-20 | Amano Pharmaceut Co Ltd | トリテルペンアルコ−ル有機酸エステル及びその製造法 |
-
1974
- 1974-02-26 GB GB871274A patent/GB1452794A/en not_active Expired
-
1975
- 1975-01-01 AR AR257778A patent/AR206704A1/es active
- 1975-02-04 FR FR7503357A patent/FR2261775B1/fr not_active Expired
- 1975-02-11 CH CH171975A patent/CH614218A5/xx not_active IP Right Cessation
- 1975-02-21 ES ES434961A patent/ES434961A1/es not_active Expired
- 1975-02-25 CA CA220,864A patent/CA1062699A/fr not_active Expired
- 1975-02-25 BR BR1131/75A patent/BR7501131A/pt unknown
- 1975-02-25 LU LU71909A patent/LU71909A1/xx unknown
- 1975-02-25 IE IE384/75A patent/IE40689B1/xx unknown
- 1975-02-25 IT IT20627/75A patent/IT1048803B/it active
- 1975-02-25 SE SE7502107A patent/SE419091B/xx not_active IP Right Cessation
- 1975-02-26 BE BE153773A patent/BE826016A/xx unknown
- 1975-02-26 JP JP50024452A patent/JPS5842199B2/ja not_active Expired
- 1975-02-26 NL NLAANVRAGE7502299,A patent/NL180108C/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| SE7502107L (en:Method) | 1975-08-27 |
| SE419091B (sv) | 1981-07-13 |
| NL180108B (nl) | 1986-08-01 |
| GB1452794A (en) | 1976-10-13 |
| ES434961A1 (es) | 1976-12-16 |
| IE40689B1 (en) | 1979-08-01 |
| BR7501131A (pt) | 1975-12-02 |
| NL7502299A (nl) | 1975-08-28 |
| BE826016A (fr) | 1975-06-16 |
| FR2261775B1 (en:Method) | 1980-05-16 |
| NL180108C (nl) | 1987-01-02 |
| CH614218A5 (en) | 1979-11-15 |
| AR206704A1 (es) | 1976-08-13 |
| JPS50142555A (en:Method) | 1975-11-17 |
| IE40689L (en) | 1975-08-26 |
| LU71909A1 (en:Method) | 1975-08-20 |
| IT1048803B (it) | 1980-12-20 |
| CA1062699A (fr) | 1979-09-18 |
| FR2261775A1 (en:Method) | 1975-09-19 |
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