ES420326A1 - P-biphenylyl esters of 15-substituted-16,17,18,19,20-pentanor prostaglandins - Google Patents
P-biphenylyl esters of 15-substituted-16,17,18,19,20-pentanor prostaglandinsInfo
- Publication number
- ES420326A1 ES420326A1 ES420326A ES420326A ES420326A1 ES 420326 A1 ES420326 A1 ES 420326A1 ES 420326 A ES420326 A ES 420326A ES 420326 A ES420326 A ES 420326A ES 420326 A1 ES420326 A1 ES 420326A1
- Authority
- ES
- Spain
- Prior art keywords
- formula
- alpha
- beta
- integer
- defined above
- 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
- 150000003180 prostaglandins Chemical class 0.000 title abstract 2
- 150000002148 esters Chemical class 0.000 title 1
- 229940094443 oxytocics prostaglandins Drugs 0.000 title 1
- -1 alpha-naphthyl Chemical group 0.000 abstract 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 abstract 1
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 229930194542 Keto Natural products 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 239000004305 biphenyl Substances 0.000 abstract 1
- YXVFYQXJAXKLAK-UHFFFAOYSA-N biphenyl-4-ol Chemical compound C1=CC(O)=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-N 0.000 abstract 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 abstract 1
- 239000012374 esterification agent Substances 0.000 abstract 1
- 125000001475 halogen functional group Chemical group 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 125000000468 ketone group Chemical group 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D309/10—Oxygen atoms
- C07D309/12—Oxygen atoms only hydrogen atoms and one oxygen atom directly attached to ring carbon atoms, e.g. tetrahydropyranyl ethers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
- C07D317/54—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/54—Quaternary phosphonium compounds
- C07F9/5407—Acyclic saturated phosphonium compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Furan Compounds (AREA)
- Pyrane Compounds (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
Abstract
A process for preparing p-biphenyl esters of ω pentanorprostaglandins substituted at position 15 of the formula **(See formula)** where A is: Ar (CH2) n- or - (CH2) m-OR2, where n is an integer from 0 to 5 when Z is a single bond, and n is an integer from 1 to 5 when Z is a bond double trans; m is an integer from 2 to 3, R2 is lower alkyl, Ar is alpha-furyl, beta-furyl, alpha-thienyl, beta-thienyl, alpha-naphthyl, beta-naphthyl, 3,4-dimethoxyphenyl, 3,4- methylenedioxyphenyl, 3,4,5-trimethoxyphenyl, or monosubstituted phenyl wherein said substituent is halo, trifluoromethyl, phenyl-lower alcohol or lower alkoxy; R1 is para-biphenyl; R is hydrogen or lower alcohol; W is a single tie or a double cis tie; Z is a single ligation or a double trans ligation; L and N form a single bond or L is hydrogen when N is alpha-hydroxyl; M is keto, **(See formula)** and wherein L, M and N are selected to complete the structure of a series A, E or F prostaglandin; characterized by reacting a compound of the formula **(See formula)** where A, Ar, R, M, L, W and Z are as defined above, N'is N as defined above or is -OTHP, and R3 is -OH or -OTHP, with p-phenylphenol in presence of a suitable esterification agent, and subsequently removing any THP groups, to obtain a compound of Formula I as defined above. (Machine-translation by Google Translate, not legally binding)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US30481572A | 1972-11-08 | 1972-11-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES420326A1 true ES420326A1 (en) | 1976-03-16 |
Family
ID=23178143
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES420326A Expired ES420326A1 (en) | 1972-11-08 | 1973-11-07 | P-biphenylyl esters of 15-substituted-16,17,18,19,20-pentanor prostaglandins |
| ES434687A Expired ES434687A1 (en) | 1972-11-08 | 1975-02-13 | P-biphenylyl esters of 15-substituted-16,17,18,19,20-pentanor prostaglandins |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES434687A Expired ES434687A1 (en) | 1972-11-08 | 1975-02-13 | P-biphenylyl esters of 15-substituted-16,17,18,19,20-pentanor prostaglandins |
Country Status (24)
| Country | Link |
|---|---|
| JP (1) | JPS5644068B2 (en) |
| AR (2) | AR204816A1 (en) |
| AT (1) | AT347607B (en) |
| BE (1) | BE807047A (en) |
| CA (1) | CA1027559A (en) |
| CH (1) | CH601222A5 (en) |
| CS (1) | CS188175B2 (en) |
| DD (2) | DD111370A5 (en) |
| DE (2) | DE2365999A1 (en) |
| ES (2) | ES420326A1 (en) |
| FI (1) | FI58116C (en) |
| FR (2) | FR2205339B1 (en) |
| GB (1) | GB1456511A (en) |
| HU (2) | HU171818B (en) |
| IE (1) | IE39686B1 (en) |
| IL (1) | IL43553A (en) |
| IN (1) | IN139905B (en) |
| NL (1) | NL7315240A (en) |
| NO (2) | NO145437C (en) |
| PH (2) | PH15504A (en) |
| SE (2) | SE420198B (en) |
| SU (2) | SU538659A3 (en) |
| YU (2) | YU287973A (en) |
| ZA (1) | ZA738593B (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2361381A1 (en) * | 1972-07-13 | 1978-03-10 | Pfizer | (15)-(Hetero) aryl prostaglandin analogues - with long-lasting prostaglandin-like activity |
| US3929862A (en) * | 1974-01-08 | 1975-12-30 | Upjohn Co | Substituted tolylesters of PGF{HD 2{B {60 |
| US3998869A (en) * | 1974-11-14 | 1976-12-21 | The Upjohn Company | Substituted anilide esters of 16-substituted PGE2 |
| DE2737807A1 (en) * | 1976-08-27 | 1978-03-09 | Pfizer | C LOW 1 -P-BIPHENYLESTER OF OMEGA-PENTANORPROSTAGLANDINES |
| US6531504B2 (en) * | 2001-05-17 | 2003-03-11 | Allergan, Inc. | Prostanoic acid derivatives as agents for lowering intraocular pressure |
-
1973
- 1973-01-01 AR AR250900A patent/AR204816A1/en active
- 1973-11-01 GB GB5088973A patent/GB1456511A/en not_active Expired
- 1973-11-01 SE SE7314885A patent/SE420198B/en unknown
- 1973-11-02 IL IL43553A patent/IL43553A/en unknown
- 1973-11-03 DE DE2365999A patent/DE2365999A1/en not_active Withdrawn
- 1973-11-03 DE DE19732355042 patent/DE2355042A1/en not_active Withdrawn
- 1973-11-06 IN IN2443/CAL/73A patent/IN139905B/en unknown
- 1973-11-07 NO NO4290/73A patent/NO145437C/en unknown
- 1973-11-07 AT AT937173A patent/AT347607B/en not_active IP Right Cessation
- 1973-11-07 FI FI3444/73A patent/FI58116C/en active
- 1973-11-07 YU YU02879/73A patent/YU287973A/en unknown
- 1973-11-07 NL NL7315240A patent/NL7315240A/xx not_active Application Discontinuation
- 1973-11-07 ES ES420326A patent/ES420326A1/en not_active Expired
- 1973-11-07 CA CA185,201A patent/CA1027559A/en not_active Expired
- 1973-11-08 DD DD174537A patent/DD111370A5/xx unknown
- 1973-11-08 CH CH1570273A patent/CH601222A5/xx not_active IP Right Cessation
- 1973-11-08 DD DD180196*A patent/DD113211A5/xx unknown
- 1973-11-08 ZA ZA738593A patent/ZA738593B/en unknown
- 1973-11-08 JP JP12501173A patent/JPS5644068B2/ja not_active Expired
- 1973-11-08 CS CS737670A patent/CS188175B2/en unknown
- 1973-11-08 HU HU73PI00000400A patent/HU171818B/en unknown
- 1973-11-08 BE BE1005489A patent/BE807047A/en unknown
- 1973-11-08 FR FR7339759A patent/FR2205339B1/fr not_active Expired
- 1973-11-08 HU HU73PI00000453A patent/HU171945B/en unknown
- 1973-11-08 PH PH15198A patent/PH15504A/en unknown
- 1973-11-08 IE IE2013/73A patent/IE39686B1/en unknown
- 1973-11-11 SU SU1971421A patent/SU538659A3/en active
-
1974
- 1974-07-31 AR AR254983A patent/AR202311A1/en active
- 1974-10-03 NO NO743588A patent/NO146280C/en unknown
-
1975
- 1975-02-13 ES ES434687A patent/ES434687A1/en not_active Expired
- 1975-03-20 SU SU752115232A patent/SU1021340A3/en active
- 1975-08-18 FR FR7525565A patent/FR2275452A1/en active Granted
-
1976
- 1976-03-12 PH PH18199A patent/PH13794A/en unknown
-
1977
- 1977-04-15 SE SE7704369A patent/SE7704369L/en not_active Application Discontinuation
-
1980
- 1980-10-15 YU YU02644/80A patent/YU264480A/en unknown
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