SU1021340A3 - Process for preparing prostaglandines - Google Patents
Process for preparing prostaglandines Download PDFInfo
- Publication number
- SU1021340A3 SU1021340A3 SU752115232A SU2115232A SU1021340A3 SU 1021340 A3 SU1021340 A3 SU 1021340A3 SU 752115232 A SU752115232 A SU 752115232A SU 2115232 A SU2115232 A SU 2115232A SU 1021340 A3 SU1021340 A3 SU 1021340A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- formula
- compounds
- oxo
- single bond
- hydroxy
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims 2
- 125000003259 prostaglandin group Chemical group 0.000 title 1
- 229940094443 oxytocics prostaglandins Drugs 0.000 claims abstract 4
- 150000003180 prostaglandins Chemical class 0.000 claims abstract 4
- RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 claims 1
- 229910000071 diazene Inorganic materials 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract 11
- -1 3,4-methylenedioxyphenyl Chemical group 0.000 abstract 4
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 230000001590 oxidative effect Effects 0.000 abstract 3
- 150000002148 esters Chemical class 0.000 abstract 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 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
- 239000002253 acid Substances 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 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
- 239000000969 carrier Substances 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- XEYBRNLFEZDVAW-ARSRFYASSA-N dinoprostone Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O XEYBRNLFEZDVAW-ARSRFYASSA-N 0.000 abstract 1
- 150000002170 ethers Chemical class 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 238000001990 intravenous administration Methods 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 230000000144 pharmacologic effect Effects 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 That Contain Two Or More Ring Oxygen Atoms (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Furan Compounds (AREA)
- Pyrane Compounds (AREA)
Abstract
1456511 Prostaglandins PFIZER Inc 1 Nov 1973 [8 Nov 1972] 50889/73 Heading C2C The invention comprises prostaglandins of the formula I and the C 15 epimers thereof, wherein A is Ar(CH 2 ) n - or -(CH 2 ) m -OR<SP>2</SP>, W is a single bond or cis double bond, Z is a single bond or trans double bond; m is oxo or n is 0 to 5 when Z is a single bond, or n is 1 to 5 when Z is a trans double bond; m is 2 or 3; R<SP>2</SP> is C 1-4 alkyl; Ar is α- or #-furyl, α- or #-thienyl, α- or #-naphthyl, 3,4-dimethoxyphenyl, 3,4-methylenedioxyphenyl, 3,4,5-trimethoxyphenyl or phenyl optionally monosubstituted by halogen, trifluoromethyl, phenyl, C 1-4 alkyl or C 1-4 alkoxy; R 1 is p-biphenylyl, R is H or C 1-4 alkyl, X and Y together form a single bond or X is H and Y is alpha-hydroxy, with the proviso that when X and Y form a single bond m is oxo; and compounds of the Formulµ II, III and VI or and their C 15 epimers, wherein m is oxo or Compounds of Formula I above are obtained by esterifying the corresponding acids of Formula I in which R<SP>1</SP> and X are hydrogen and Y is alpha-hydroxy with p-phenylphenol, and if desired, dehydrating the resulting compounds in which m is oxo and Y is alpha-hydroxy. The esters of the prostaglandin E and F series may also be obtained by hydrolysing the corresponding 11,15-bis-(tetrahydropyranyl) ethers of Formula VI above which are obtained by reacting compounds of the Formula VII with compounds of the formula and if desired, oxidizing and/or hydrogenating the resulting compounds of formula VI above in which m is Compounds of Formula II and III above are obtained by reacting compounds of formula VII above with compounds of the formula and if desired, oxidizing and/or hydrogenating the resulting compounds of Formula II above. Biphenylyl 9,15 - dioxo - 11α - hydroxy - 17- phenyl - 18,19,20 - trinor - cis - 5, trans - 13- prostadienoate is obtained by oxidizing biphenylyl 9 - oxo - 11α,15# - dihydroxy - 17- phenyl - 18,19,20 - trinor - cis - 5, trans - 13- prostadienoate with manganese dioxide. Pharmaceutical compositions, suitable for oral, intravaginal, intraamniotically, intravenous or intranasal administration, contain the above esters of Formula I together with suitable carriers or diluents. The compound possess similar pharmacological properties to those of the naturally occurring prostaglandins. Reference has been directed by the Comptroller to Specifications 1,386,146, 1,345,934 and 1,324,737.
Description
tctc
со with
i 1 ,i 1,
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US30481572A | 1972-11-08 | 1972-11-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU1021340A3 true SU1021340A3 (en) | 1983-05-30 |
Family
ID=23178143
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1971421A SU538659A3 (en) | 1972-11-08 | 1973-11-11 | Method for producing compounds of prostaglandins |
| SU752115232A SU1021340A3 (en) | 1972-11-08 | 1975-03-20 | Process for preparing prostaglandines |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1971421A SU538659A3 (en) | 1972-11-08 | 1973-11-11 | Method for producing compounds of 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) | DD113211A5 (en) |
| DE (2) | DE2355042A1 (en) |
| ES (2) | ES420326A1 (en) |
| FI (1) | FI58116C (en) |
| FR (2) | FR2205339B1 (en) |
| GB (1) | GB1456511A (en) |
| HU (2) | HU171945B (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 |
|---|---|---|---|---|
| FR2361410A1 (en) * | 1972-07-13 | 1978-03-10 | Pfizer | DIALKYL ALKYLPHOSPHONATES, USEFUL AS PROSTAGLANDIN SYNTHESIS INTERMEDIARIES |
| 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 SE SE7314885A patent/SE420198B/en unknown
- 1973-11-01 GB GB5088973A patent/GB1456511A/en not_active Expired
- 1973-11-02 IL IL43553A patent/IL43553A/en unknown
- 1973-11-03 DE DE19732355042 patent/DE2355042A1/en not_active Withdrawn
- 1973-11-03 DE DE2365999A patent/DE2365999A1/en not_active Withdrawn
- 1973-11-06 IN IN2443/CAL/73A patent/IN139905B/en unknown
- 1973-11-07 ES ES420326A patent/ES420326A1/en not_active Expired
- 1973-11-07 YU YU02879/73A patent/YU287973A/en unknown
- 1973-11-07 AT AT937173A patent/AT347607B/en not_active IP Right Cessation
- 1973-11-07 NL NL7315240A patent/NL7315240A/xx not_active Application Discontinuation
- 1973-11-07 NO NO4290/73A patent/NO145437C/en unknown
- 1973-11-07 FI FI3444/73A patent/FI58116C/en active
- 1973-11-07 CA CA185,201A patent/CA1027559A/en not_active Expired
- 1973-11-08 DD DD180196*A patent/DD113211A5/xx unknown
- 1973-11-08 IE IE2013/73A patent/IE39686B1/en unknown
- 1973-11-08 JP JP12501173A patent/JPS5644068B2/ja not_active Expired
- 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 ZA ZA738593A patent/ZA738593B/en unknown
- 1973-11-08 HU HU73PI00000400A patent/HU171818B/en unknown
- 1973-11-08 DD DD174537A patent/DD111370A5/xx unknown
- 1973-11-08 CS CS737670A patent/CS188175B2/en unknown
- 1973-11-08 PH PH15198A patent/PH15504A/en unknown
- 1973-11-08 CH CH1570273A patent/CH601222A5/xx not_active IP Right Cessation
- 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
Non-Patent Citations (1)
| Title |
|---|
| 1. Вейганд-Хипьгетаг. Методы эксперимента в органической хнмни. М., Хими , 1968, с. 347. * |
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