GB1111752A - A novel acid anhydride,process for the manufacture and use thereof - Google Patents
A novel acid anhydride,process for the manufacture and use thereofInfo
- Publication number
- GB1111752A GB1111752A GB89966A GB89966A GB1111752A GB 1111752 A GB1111752 A GB 1111752A GB 89966 A GB89966 A GB 89966A GB 89966 A GB89966 A GB 89966A GB 1111752 A GB1111752 A GB 1111752A
- Authority
- GB
- United Kingdom
- Prior art keywords
- testosterone
- hydroxy
- androstene
- ethinyl
- vinyl
- 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
- 238000000034 method Methods 0.000 title abstract 2
- 150000008065 acid anhydrides Chemical class 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 abstract 6
- JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 abstract 6
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 abstract 4
- MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testostosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 abstract 4
- 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 abstract 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 4
- 150000008064 anhydrides Chemical class 0.000 abstract 3
- 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 abstract 3
- 229960000890 hydrocortisone Drugs 0.000 abstract 3
- 238000002360 preparation method Methods 0.000 abstract 3
- BNUOCVTVOYWNJC-HYURVVLDSA-N (8r,9s,10r,13s,14s)-10,13,17-trimethyl-1,2,3,6,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthrene-3,17-diol Chemical compound C1CC2=CC(O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CCC(C)(O)[C@@]1(C)CC2 BNUOCVTVOYWNJC-HYURVVLDSA-N 0.000 abstract 2
- GCKMFJBGXUYNAG-UHFFFAOYSA-N 17alpha-methyltestosterone Natural products C1CC2=CC(=O)CCC2(C)C2C1C1CCC(C)(O)C1(C)CC2 GCKMFJBGXUYNAG-UHFFFAOYSA-N 0.000 abstract 2
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 abstract 2
- -1 Alkali metal salts Chemical class 0.000 abstract 2
- GCKMFJBGXUYNAG-HLXURNFRSA-N Methyltestosterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@](C)(O)[C@@]1(C)CC2 GCKMFJBGXUYNAG-HLXURNFRSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 abstract 2
- 235000012000 cholesterol Nutrition 0.000 abstract 2
- 230000032050 esterification Effects 0.000 abstract 2
- 238000005886 esterification reaction Methods 0.000 abstract 2
- 150000004820 halides Chemical class 0.000 abstract 2
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 abstract 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 2
- 229960001566 methyltestosterone Drugs 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 238000000926 separation method Methods 0.000 abstract 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 2
- 229960003604 testosterone Drugs 0.000 abstract 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 2
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 abstract 1
- DNXHEGUUPJUMQT-UHFFFAOYSA-N (+)-estrone Natural products OC1=CC=C2C3CCC(C)(C(CC4)=O)C4C3CCC2=C1 DNXHEGUUPJUMQT-UHFFFAOYSA-N 0.000 abstract 1
- 239000001490 (3R)-3,7-dimethylocta-1,6-dien-3-ol Substances 0.000 abstract 1
- DSQNUORSFQNUMX-PWKGVDONSA-N (8S,9S,10S,11S,13S,14S)-11-hydroxy-10,13-dimethyl-2,4,5,6,7,8,9,11,12,14-decahydro-1H-cyclopenta[a]phenanthrene-3,17-dione Chemical class O[C@@H]1[C@@H]2[C@]3(CCC(CC3CC[C@H]2[C@@H]2C=CC([C@@]2(C)C1)=O)=O)C DSQNUORSFQNUMX-PWKGVDONSA-N 0.000 abstract 1
- IATKKATWPOVYCC-VMXHOPILSA-N (8s,9s,10r,13s,14s)-10,13-dimethyl-2,3,6,7,8,9,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthrene Chemical compound C1CC2=CCCC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CCC[C@@]1(C)CC2 IATKKATWPOVYCC-VMXHOPILSA-N 0.000 abstract 1
- CDOSHBSSFJOMGT-JTQLQIEISA-N (R)-linalool Natural products CC(C)=CCC[C@@](C)(O)C=C CDOSHBSSFJOMGT-JTQLQIEISA-N 0.000 abstract 1
- 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 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 1
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 abstract 1
- 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 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 abstract 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 abstract 1
- 244000028419 Styrax benzoin Species 0.000 abstract 1
- 235000000126 Styrax benzoin Nutrition 0.000 abstract 1
- 235000008411 Sumatra benzointree Nutrition 0.000 abstract 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- AEMFNILZOJDQLW-QAGGRKNESA-N androst-4-ene-3,17-dione Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 AEMFNILZOJDQLW-QAGGRKNESA-N 0.000 abstract 1
- 239000006286 aqueous extract Substances 0.000 abstract 1
- 239000002585 base Substances 0.000 abstract 1
- 229960002130 benzoin Drugs 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 229940107161 cholesterol Drugs 0.000 abstract 1
- 239000013078 crystal Substances 0.000 abstract 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 abstract 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 229960005309 estradiol Drugs 0.000 abstract 1
- 229930182833 estradiol Natural products 0.000 abstract 1
- 229960003399 estrone Drugs 0.000 abstract 1
- 235000019382 gum benzoic Nutrition 0.000 abstract 1
- 238000002955 isolation Methods 0.000 abstract 1
- 229930007744 linalool Natural products 0.000 abstract 1
- 229940041616 menthol Drugs 0.000 abstract 1
- UJQMLHKSZKBMMO-UHFFFAOYSA-N n,n-diethylethanamine;pyridine Chemical compound C1=CC=NC=C1.CCN(CC)CC UJQMLHKSZKBMMO-UHFFFAOYSA-N 0.000 abstract 1
- VOJYZDFYEHKHAP-XGXHKTLJSA-N norvinisterone Chemical compound O=C1CC[C@@H]2[C@H]3CC[C@](C)([C@](CC4)(O)C=C)[C@@H]4[C@@H]3CCC2=C1 VOJYZDFYEHKHAP-XGXHKTLJSA-N 0.000 abstract 1
- 229940067107 phenylethyl alcohol Drugs 0.000 abstract 1
- 229910052700 potassium Inorganic materials 0.000 abstract 1
- 239000011591 potassium Substances 0.000 abstract 1
- 159000000001 potassium salts Chemical class 0.000 abstract 1
- 150000003138 primary alcohols Chemical class 0.000 abstract 1
- 229960004063 propylene glycol Drugs 0.000 abstract 1
- 235000013772 propylene glycol Nutrition 0.000 abstract 1
- 238000000746 purification Methods 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 238000007127 saponification reaction Methods 0.000 abstract 1
- 150000003333 secondary alcohols Chemical class 0.000 abstract 1
- 229920002554 vinyl polymer Polymers 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C55/00—Saturated compounds having more than one carboxyl group bound to acyclic carbon atoms
- C07C55/02—Dicarboxylic acids
- C07C55/06—Oxalic acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/34—Esters of acyclic saturated polycarboxylic acids having an esterified carboxyl group bound to an acyclic carbon atom
- C07C69/36—Oxalic acid esters
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Steroid Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEO0010600 | 1965-01-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1111752A true GB1111752A (en) | 1968-05-01 |
Family
ID=7352036
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB89966A Expired GB1111752A (en) | 1965-01-15 | 1966-01-07 | A novel acid anhydride,process for the manufacture and use thereof |
Country Status (4)
| Country | Link |
|---|---|
| DE (1) | DE1593190A1 (enrdf_load_stackoverflow) |
| FR (1) | FR1466671A (enrdf_load_stackoverflow) |
| GB (1) | GB1111752A (enrdf_load_stackoverflow) |
| NL (1) | NL6600508A (enrdf_load_stackoverflow) |
-
1965
- 1965-01-15 DE DE19651593190 patent/DE1593190A1/de active Pending
-
1966
- 1966-01-07 GB GB89966A patent/GB1111752A/en not_active Expired
- 1966-01-12 FR FR45580A patent/FR1466671A/fr not_active Expired
- 1966-01-14 NL NL6600508A patent/NL6600508A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NL6600508A (enrdf_load_stackoverflow) | 1966-07-18 |
| DE1593190A1 (de) | 1970-04-30 |
| FR1466671A (fr) | 1967-01-20 |
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