FR2230620A1 - Prepn. of prostanoic esters - by addition of an alcohol to a prostanoic acid mixed anhydride - Google Patents
Prepn. of prostanoic esters - by addition of an alcohol to a prostanoic acid mixed anhydrideInfo
- Publication number
- FR2230620A1 FR2230620A1 FR7318656A FR7318656A FR2230620A1 FR 2230620 A1 FR2230620 A1 FR 2230620A1 FR 7318656 A FR7318656 A FR 7318656A FR 7318656 A FR7318656 A FR 7318656A FR 2230620 A1 FR2230620 A1 FR 2230620A1
- Authority
- FR
- France
- Prior art keywords
- prostanoic
- beta
- pyrrolidino
- piperidino
- prepn
- 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.)
- Withdrawn
Links
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 title abstract 2
- 150000008064 anhydrides Chemical class 0.000 title abstract 2
- 150000002148 esters Chemical class 0.000 title abstract 2
- WGJJROVFWIXTPA-OALUTQOASA-N prostanoic acid Chemical compound CCCCCCCC[C@H]1CCC[C@@H]1CCCCCCC(O)=O WGJJROVFWIXTPA-OALUTQOASA-N 0.000 title 1
- -1 or beta-pyrrolidino Chemical group 0.000 abstract 3
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 abstract 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 125000003342 alkenyl group Chemical group 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 2
- 125000006203 morpholinoethyl group Chemical group [H]C([H])(*)C([H])([H])N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 0.000 abstract 2
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 abstract 1
- 150000008041 alkali metal carbonates Chemical class 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000000392 cycloalkenyl group Chemical group 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C405/00—Compounds containing a five-membered ring having two side-chains in ortho position to each other, and having oxygen atoms directly attached to the ring in ortho position to one of the side-chains, one side-chain containing, not directly attached to the ring, a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, and the other side-chain having oxygen atoms attached in gamma-position to the ring, e.g. prostaglandins ; Analogues or derivatives thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Prostanoic esters of formula (I): (where A =-CH2)3-, -COCH=CH-, -CO-CH2CH-, OH or (I) -CH-CH2-CH-OH OH OH; R and R1 + H, CH3 or C2H5; R11 = a residue having is not >11C atoms which is alkyl, alkenyl, cycloalkyl, aralkyl, gamma-dialkylaminoethyl, beta-dialkylaminoproyl, gamma-pyrrolidino, piperidino or morpholinoethyl, or beta-pyrrolidino, piperidino or morpholinoethyl, or beta-pyrrolidino, piperidino or morpholinopropyl; Y = -(CH2)3-, -CH2CH2CHOH-, CH=CH-CH-, =CH-CH-CH- or CH2CH2CO-; OH OH Z =-CH2CH2 or -CH=CH- and is a bond in the alpha- or beta-configuration), are prepd, by treating an alcohol R11OH in the presence of an acid acceptor with a mixed anhydride of formula (II): (where X is -C-OR111 and R111 = alkyl, alkenyl, cycloalkyl, cycloalkenyl, aryl or aralkyl of up to 10C). Cpds. (I), where R and/or R1 are other than H and R11 is other man alkyl, are now. (I) haven known pharmaceutical activity. The prepn. is easier than known methods. The acid acceptor is pref. a tret. amine or an alkali metal carbonate. The reaction is effected in a liq. medium such a hydrocarbon, which may be halogenated, an ether, O-heterocycle, an N,N-dicarboxamide or a mixt. of these. The reaction temp. is pref. below ambient.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7318656A FR2230620A1 (en) | 1973-05-23 | 1973-05-23 | Prepn. of prostanoic esters - by addition of an alcohol to a prostanoic acid mixed anhydride |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7318656A FR2230620A1 (en) | 1973-05-23 | 1973-05-23 | Prepn. of prostanoic esters - by addition of an alcohol to a prostanoic acid mixed anhydride |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| FR2230620A1 true FR2230620A1 (en) | 1974-12-20 |
Family
ID=9119807
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR7318656A Withdrawn FR2230620A1 (en) | 1973-05-23 | 1973-05-23 | Prepn. of prostanoic esters - by addition of an alcohol to a prostanoic acid mixed anhydride |
Country Status (1)
| Country | Link |
|---|---|
| FR (1) | FR2230620A1 (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2010505808A (en) * | 2006-10-02 | 2010-02-25 | テックフィールズ バイオケム カンパニー リミテッド | Positively charged water-soluble prodrugs of prostaglandins and related compounds with very high skin permeability |
| JP2013231038A (en) * | 2013-06-04 | 2013-11-14 | Techfields Biochem Co Ltd | Positively charged water-soluble prodrug of prostaglandin and related compound having very high skin-penetration rate |
| JP2015134801A (en) * | 2015-03-09 | 2015-07-27 | テックフィールズ バイオケム カンパニー リミテッド | Prostaglandin and positively charged water-soluble prodrug of related compound having very high skin penetration rate |
-
1973
- 1973-05-23 FR FR7318656A patent/FR2230620A1/en not_active Withdrawn
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2010505808A (en) * | 2006-10-02 | 2010-02-25 | テックフィールズ バイオケム カンパニー リミテッド | Positively charged water-soluble prodrugs of prostaglandins and related compounds with very high skin permeability |
| US11555014B2 (en) | 2006-10-02 | 2023-01-17 | Techfields Pharma Co., Ltd. | High penetration prodrug compositions of prostaglandins and related compounds |
| JP2013231038A (en) * | 2013-06-04 | 2013-11-14 | Techfields Biochem Co Ltd | Positively charged water-soluble prodrug of prostaglandin and related compound having very high skin-penetration rate |
| JP2015134801A (en) * | 2015-03-09 | 2015-07-27 | テックフィールズ バイオケム カンパニー リミテッド | Prostaglandin and positively charged water-soluble prodrug of related compound having very high skin penetration rate |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |