GB1440361A - 11-deoxyprostaglandins of the e and f series and the preparation thereof - Google Patents
11-deoxyprostaglandins of the e and f series and the preparation thereofInfo
- Publication number
- GB1440361A GB1440361A GB2583673A GB2583673A GB1440361A GB 1440361 A GB1440361 A GB 1440361A GB 2583673 A GB2583673 A GB 2583673A GB 2583673 A GB2583673 A GB 2583673A GB 1440361 A GB1440361 A GB 1440361A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- compounds
- vinylene
- mercapto
- formula
- 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
- 125000000217 alkyl group Chemical group 0.000 abstract 17
- 150000001875 compounds Chemical class 0.000 abstract 16
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 4
- -1 cyano, carbamoyl Chemical group 0.000 abstract 4
- 229940094443 oxytocics prostaglandins Drugs 0.000 abstract 4
- 150000003180 prostaglandins Chemical class 0.000 abstract 4
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 abstract 4
- 125000004414 alkyl thio group Chemical group 0.000 abstract 3
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 abstract 2
- 239000005977 Ethylene Substances 0.000 abstract 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 2
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 abstract 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 abstract 2
- 230000003301 hydrolyzing effect Effects 0.000 abstract 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 abstract 2
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 abstract 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- MWFMGBPGAXYFAR-UHFFFAOYSA-N 2-hydroxy-2-methylpropanenitrile Chemical compound CC(C)(O)C#N MWFMGBPGAXYFAR-UHFFFAOYSA-N 0.000 abstract 1
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 abstract 1
- 241000219210 Plexaura homomalla Species 0.000 abstract 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 abstract 1
- 125000004423 acyloxy group Chemical group 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000003282 alkyl amino group Chemical group 0.000 abstract 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- OPHUWKNKFYBPDR-UHFFFAOYSA-N copper lithium Chemical compound [Li].[Cu] OPHUWKNKFYBPDR-UHFFFAOYSA-N 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- 230000000911 decarboxylating effect Effects 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- GDTSOICKGZVOCQ-UHFFFAOYSA-N lithium perhydro-9b-boraphenalylhydride Chemical compound [Li].C1CCC2CCCC3B2C1CCC3 GDTSOICKGZVOCQ-UHFFFAOYSA-N 0.000 abstract 1
- 150000004702 methyl esters Chemical class 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 230000000144 pharmacologic effect Effects 0.000 abstract 1
- 150000003839 salts Chemical class 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
-
- 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
- C07C405/0008—Analogues having the carboxyl group in the side-chains replaced by other functional groups
- C07C405/0033—Analogues having the carboxyl group in the side-chains replaced by other functional groups containing sulfur
-
- 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
- C07C405/0008—Analogues having the carboxyl group in the side-chains replaced by other functional groups
- C07C405/0041—Analogues having the carboxyl group in the side-chains replaced by other functional groups containing nitrogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1440361 Prostaglandins AMERICAN CYANAMID CO 30 May 1973 [24 July 1972 17 Nov 1972] 25836/73 Heading C2C The invention comprises prostaglandins of the Formula A wherein R 1 is C 1-4 alkyl, C 2-4 (1-alkenyl), C 1-4 alkylthio, C 2-4 alkanoylthio, #-di(C 1-4 alkyl)- amino-C 1-4 alkylthio, cyano, carbamoyl, carboxy or C 2-4 alkoxycarbonyl, α-nitro-C 1-4 alkyl, αα - di(alkoxy - carbonyl) - C 1-4 alkyl, αα- dicarboxy - C 1-4 alkyl, α - carboxy - C 1-4 alkyl, S<SP>(+)</SP>(R 4 ) 3 X<SP>(-)</SP>, where R 4 is C 1-4 alkyl and X is halogen, p-toluenesulphonyloxy or C 1-4 alkylsulphonyloxy, formyl, αα-di(C 1-4 alkoxy)methyl, or mercapto; R 2 is hydroxy, C 1-4 alkanoyloxy, C 1-4 alkylsulphonyloxy, or C 1-4 alkyl, with the proviso that when R 2 is C 1-4 alkyl then R 1 is the same C 1-4 alkyl group; R 3 is H or C 1-12 alkyl; Y is >C=O, with the proviso that when Y is carbonyl then R 1 is not mercapto; the radical -C 5 -C 6 - is ethylene or cis-vinylene, and the radical -C 13 -C 14 - is ethylene or trans-vinylene, with the proviso that when -C 5 -C 6 - is cis-vinylene then -C 13 -C 14 - must be trans-vinylene, and phamaceutically acceptable salts thereof when R 3 is H. The compounds of Formula A in which R 2 is hydroxy or C 1-4 alkyl and R 1 is as defined above except than R 1 cannot be mercapto are prepared by reacting compounds of the formula wherein Z is H or acetyl with (R 4 ) 2 CuLi, R 6 CH(CO 2 R 7 ) 2 , R 6 CH 2 NO 2 , R 5 SH or acetone cyanohydrin in the presence of alkaline catalysts, where R 4 is C 1-4 alkyl, C 2-4 (1-alkenyl), R 5 is #-di(C 1-4 alkylamino)alkyl, C 1-4 alkyl, or C 1-4 alkanoyl, R 6 is H or C 1-4 alkyl, and R 7 is C 1-4 alkyl and when necessary or desired, hydrolysing, and, if desired decarboxylating the resulting compounds in which R 1 is α,α-di(alkoxycarbonyl)alkyl, or converting compounds in which R 1 is C 1-4 alkylthio, into compounds in which R 1 is S<SP>(+)</SP>(R 4 ) 2 X<SP>(-)</SP> by reacting them with alkyl halides alkyl p-toluene-sulphonates or alkyl alkylsulphonates, and when necessary or desired hydrolysing compounds in which R 1 is cyano to give compounds in which R 1 is carbamoyl, which in turn may be hydrolysed to give compounds in which R 1 is carboxy and then, if desired, esterified, and when necessary converting compounds in which R 1 is nitromethyl to the corresponding compounds in which R 1 is formyl and when necessary converting these compounds into compounds in which R 1 is dialkoxymethyl, and if desired reducing the carbonyl group in the resulting compounds, and when R 2 is hydroxy inverting its configuration and if desired hydrogenating the double bonds. Compounds of Formula A above in which R 1 is mercapto and Y is are obtained by reducing the corresponding compounds in which R 1 is alkanoylthio and Y is carbonyl with lithium perhydro-9b-boraphenalyl hydride. 15 - o - Acetytprostaglandin A 2 methyl ester is obtained by extracting it from Plexaura Homomalla (esper) with isomeric hexanes. Pharmaceutical compositions contain the above prostaglandins and pharmaceutically acceptable carriers. The compounds possess similar pharmacological properties to those of naturally occurring prostaglandins. Reference has been directed by the Comptroller to Specifications 1,097,533 and 1,097,157.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/274,559 US4141914A (en) | 1972-07-24 | 1972-07-24 | Novel 11-deoxy-11-substituted prostaglandins of the E and F series |
| US30772172A | 1972-11-17 | 1972-11-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1440361A true GB1440361A (en) | 1976-06-23 |
Family
ID=26956900
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2583673A Expired GB1440361A (en) | 1972-07-24 | 1973-05-30 | 11-deoxyprostaglandins of the e and f series and the preparation thereof |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS4985052A (en) |
| DE (1) | DE2330905A1 (en) |
| FR (1) | FR2193613B1 (en) |
| GB (1) | GB1440361A (en) |
| NL (1) | NL7308633A (en) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4241221A (en) * | 1972-07-24 | 1980-12-23 | American Cyanamid Company | Novel 11-deoxy-substituted prostaglandins of the E and F series |
| US4218565A (en) * | 1972-07-24 | 1980-08-19 | American Cyanamid Company | Novel 11-deoxy-11-substituted prostaglandins of the E and F series |
| US4053467A (en) * | 1974-07-03 | 1977-10-11 | American Home Products Corporation | Prostaglandin derivatives |
| DE2629834A1 (en) | 1976-06-30 | 1978-01-12 | Schering Ag | NEW PROSTANIC ACID DERIVATIVES AND METHOD FOR THEIR PRODUCTION |
| US4325970A (en) * | 1980-10-09 | 1982-04-20 | Hoffmann-La Roche Inc. | 15-Acetyl-prostaglandins |
| US4403100A (en) * | 1981-10-30 | 1983-09-06 | The Upjohn Company | (11R)-11-Deoxy-11-alkyl-6-oxo-prostaglandins |
| US5292754A (en) * | 1990-03-08 | 1994-03-08 | Shionogi & Co., Ltd. | Treatment for hypertension or glaucoma in eyes |
| ES2069881T3 (en) * | 1990-03-08 | 1995-05-16 | Shionogi & Co | DERIVATIVE OF 15-DEOXYPROSTAGLANDINE. |
-
1973
- 1973-05-30 GB GB2583673A patent/GB1440361A/en not_active Expired
- 1973-06-18 DE DE19732330905 patent/DE2330905A1/en active Pending
- 1973-06-21 NL NL7308633A patent/NL7308633A/xx unknown
- 1973-07-24 JP JP8351873A patent/JPS4985052A/ja active Pending
- 1973-07-24 FR FR7327072A patent/FR2193613B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE2330905A1 (en) | 1974-02-07 |
| FR2193613B1 (en) | 1976-12-24 |
| AU5681373A (en) | 1974-12-12 |
| NL7308633A (en) | 1974-01-28 |
| FR2193613A1 (en) | 1974-02-22 |
| JPS4985052A (en) | 1974-08-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |