GB1439511A - N-substituted prostaglandin carboxamides - Google Patents
N-substituted prostaglandin carboxamidesInfo
- Publication number
- GB1439511A GB1439511A GB2561373A GB2561373A GB1439511A GB 1439511 A GB1439511 A GB 1439511A GB 2561373 A GB2561373 A GB 2561373A GB 2561373 A GB2561373 A GB 2561373A GB 1439511 A GB1439511 A GB 1439511A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formula
- compounds
- prostaglandins
- oxo
- single bond
- 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
- -1 prostaglandin carboxamides Chemical class 0.000 title abstract 13
- 150000001875 compounds Chemical class 0.000 abstract 20
- 150000003180 prostaglandins Chemical class 0.000 abstract 10
- 229940094443 oxytocics prostaglandins Drugs 0.000 abstract 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 6
- 150000001558 benzoic acid derivatives Chemical class 0.000 abstract 4
- 150000004675 formic acid derivatives Chemical class 0.000 abstract 4
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 230000007062 hydrolysis Effects 0.000 abstract 3
- 238000006460 hydrolysis reaction Methods 0.000 abstract 3
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- 230000003301 hydrolyzing effect Effects 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 239000000543 intermediate Substances 0.000 abstract 2
- KDZMEZRLDMNVMZ-IHWYPQMZSA-N (z)-hept-5-enamide Chemical compound C\C=C/CCCC(N)=O KDZMEZRLDMNVMZ-IHWYPQMZSA-N 0.000 abstract 1
- 125000003047 N-acetyl group Chemical group 0.000 abstract 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 abstract 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract 1
- 125000005129 aryl carbonyl group Chemical group 0.000 abstract 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 abstract 1
- 125000001589 carboacyl group Chemical group 0.000 abstract 1
- LMKPHJYTFHAGHK-UHFFFAOYSA-N cyclodrine Chemical compound C1CCCC1(O)C(C(=O)OCCN(CC)CC)C1=CC=CC=C1 LMKPHJYTFHAGHK-UHFFFAOYSA-N 0.000 abstract 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- VONWDASPFIQPDY-UHFFFAOYSA-N dimethyl methylphosphonate Chemical compound COP(C)(=O)OC VONWDASPFIQPDY-UHFFFAOYSA-N 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- PWIVQUPZVUNZKX-UHFFFAOYSA-N methyl 2,2-dimethylhexanoate Chemical compound CCCCC(C)(C)C(=O)OC PWIVQUPZVUNZKX-UHFFFAOYSA-N 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- 125000004043 oxo group Chemical group O=* 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 230000000144 pharmacologic effect Effects 0.000 abstract 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 abstract 1
- 229910000033 sodium borohydride Inorganic materials 0.000 abstract 1
- 239000012279 sodium borohydride Substances 0.000 abstract 1
- 230000000699 topical effect Effects 0.000 abstract 1
Classifications
-
- 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
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/93—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems condensed with a ring other than six-membered
- C07D307/935—Not further condensed cyclopenta [b] furans or hydrogenated cyclopenta [b] furans
-
- 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
- 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
-
- 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
- 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
- C07D333/26—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 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
- C07D333/30—Hetero atoms other than halogen
- C07D333/34—Sulfur 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 System
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids RP(=O)(OH)2; Thiophosphonic acids, i.e. RP(=X)(XH)2 (X = S, Se)
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl
-
- 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 System
- 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
Abstract
1439511 Prostaglandins; phosphonate intermediate PFIZER Inc 29 May 1973 [7 June 1972] 25613/73 Headings C2C and C2P The invention comprises prostaglandins of the Formula I wherein R is C 2 -C 8 alkanoyl, C 4-8 cycloalkanoyl, C 7-11 arylcarbonyl optionally substituted by CH 3 , OCH 3 or halogen, O 1-7 alkylsulphonyl, heteroarylsulphonyl or arylsulphonyl optionally substituted by CH 3 , OCH 3 or halogen; R 1 is H or C 1-3 alkyl; R 2 is C 5-11 alkyl; R 4 is H; W is a single bond or cis double bond; Z is a single bond or trans double bond; m is oxo or X is alpha-hydroxy and Y is H, or X and Y when taken together form a single bond, wherein M, X and Y are so selected as to complete the structure of a prostaglandin of the A, E or F series ; and the formates, alkanoates or benzoates of any free 9, 11 and 15 hydroxy groups; and prostaglandins of the Formulae V and IIc wherein THP is 2-tetrahydropyranyl and the C 9 and C 15 formates, alkanoates and benzoates of the compounds of Formula IIc. The prostaglandins of the F series of Formula I above are prepared by hydrolysing the corresponding compounds of Formula V above in which M is or compounds of Formula He with aqueous acetic acid, reducing the corresponding prostaglandins of the E series of Formula I in which M is oxo with sodium borohydride, or by the basic hydrolysis of compounds of Formula I in which W is a single bond, Z is a trans double bond, Y is H, X is alpha-hydroxy and M is The prostaglandins of the E series are obtained by hydrolysing with aqueous acetic acid the corresponding compounds of Formula V above in which M is oxo, resulting from the oxidation of the appropriate compounds of Formula V above in which M is The prostaglandins of the A series of Formula I above are made by dehydrating the corresponding prostaglandins of the E series of Formula I. Compounds of Formula V above in which M is are prepared by reacting compounds of the Formula L with compounds of the formula (C 6 H 5 ) 3 P = CH-CH 2 -CH 2 -CH 2 -CO-NHR and, if desired, hydrogenating the resulting compounds. Compounds of Formula V in which M is are obtained by reducing the corresponding compounds of Formula V in which M is oxo, or by the basic hydrolysis of compounds of Formula V above in which M is The compounds of Formula IIc above are obtained by the basic hydrolysis of the corresponding compounds of Formula I in which W is a single bond. R 4 and Y are both H, X is alpha- (2-tetrahydropyranyloxy) and M is The compounds resulting from the above processes may be acylated to give the corresponding formates, alkanoates, or benzoates, or may be hydrogenated to give the corresponding compounds in which W is a single bond and Z is a trans double bond or a single bond. The following intermediates are also prepared: compounds of Formula L above and the corresponding compounds in which both tetrahydropyranyl radicals are replaced by hydrogen atoms; 4# -benzyloxymethyl-5x-(2-tetrahydropyranyloxy) - 3,3a#,4,5,6,6a# - hexahydro- 2H - cyclopenta[b]furan - 2 - ol; 3,3a#,4,5,6,6a#- hexahydro - 2H - cyclopenta[b]furan - 2 - ones which are substituted in the 4#-position by alkyl or trans- 1 -alkenyl radicals substituted in the 3-position by oxo, hydroxy or 2-tetrahydropyranyloxy radicals and in the 5α- position by hydroxy, 2-tetrahydropyranyloxy or p - phenylbenzoyloxy radicals; N-acetyl (or methansulphonyl) - 7 - [2# - benzoloxymethyl - 3α - (2 - tetrahydropyranyloxy) - 5α- hydroxy (or acetoxy)cyclopent - 1α - yl] i cis- 5 - heptenamide, N - acetyl (or methanesulphonyl) - 7 - [2# - hydroxymethyl (or formyl) - 3x - (2 - tetrahydropyranylxoy) - 5α- acetoxycyclopent - 1α - yl] - heptanamide, N - acetyl (or methanesulphonyl) - 9α - acetoxy- 11 α - (2 - tetrahydropyranyloxy) - 15 - oxo - 13- trans - prostenamide and N - acetyl (or methanesulphonyl) - 9α - acetoxy - 11α - (2- tetrahydropyronyloxy) - 15 - oxo - 16,16- dimethyl-13-trans-prostenamide Dimethyl 2 - oxo - 3,3 - dimethylphosphonate is prepared by reacting dimethyl methylphosphonate and methyl 2,2-dimethylhexanoate in the presence of butyl lithium. Pharmaceutical compositions, suitable for oral, parenteral, topical, intranasal or intravaginal administration, contain the prostaglands of Formula I above or formates, alkanoates or benzoates thereof together with pharmaceutically acceptable carriers. The compounds possess similar pharmacological properties to those of the naturally occurring prostaglandins.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US26051872A | 1972-06-07 | 1972-06-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1439511A true GB1439511A (en) | 1976-06-16 |
Family
ID=22989486
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4209675A Expired GB1439512A (en) | 1972-06-07 | 1973-05-29 | Amidoalkyl triphenylphosphonium bromides |
| GB2561373A Expired GB1439511A (en) | 1972-06-07 | 1973-05-29 | N-substituted prostaglandin carboxamides |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4209675A Expired GB1439512A (en) | 1972-06-07 | 1973-05-29 | Amidoalkyl triphenylphosphonium bromides |
Country Status (24)
| Country | Link |
|---|---|
| JP (2) | JPS5715591B2 (en) |
| AR (1) | AR207434A1 (en) |
| AT (1) | AT340069B (en) |
| BE (1) | BE800580A (en) |
| CA (1) | CA985280A (en) |
| CH (3) | CH591511A5 (en) |
| CS (1) | CS200166B2 (en) |
| DD (2) | DD109211A5 (en) |
| DE (1) | DE2329092A1 (en) |
| ES (3) | ES415611A1 (en) |
| FI (1) | FI58327C (en) |
| FR (2) | FR2187344B1 (en) |
| GB (2) | GB1439512A (en) |
| HU (3) | HU170491B (en) |
| IE (1) | IE38058B1 (en) |
| IL (2) | IL42385A (en) |
| IN (1) | IN138966B (en) |
| LU (1) | LU67754A1 (en) |
| NL (2) | NL160814C (en) |
| NO (2) | NO146538C (en) |
| PH (2) | PH14204A (en) |
| SE (3) | SE415883B (en) |
| YU (1) | YU36498B (en) |
| ZA (1) | ZA733763B (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001058866A2 (en) * | 2000-02-08 | 2001-08-16 | Allergan, Inc. | Ocular hypotensive lipids |
| WO2002100388A2 (en) * | 2001-06-13 | 2002-12-19 | Allergan, Inc. | Cyclopentane heptan (ene) acyl sulfonamide, 2-alkyl or 2-arylalkyl, or 2-heteroarylalkenyl derivatives as therapeutic agents for the treatment of ocular hypertension |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MX3291E (en) * | 1975-04-23 | 1980-08-22 | Upjohn Co | PROCEDURE FOR PREPARING ANALOGS OF PROSTAGLANDINAS |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3187043A (en) * | 1962-05-18 | 1965-06-01 | Monsanto Co | Monohalophosphonium halides |
-
1973
- 1973-01-01 AR AR248467A patent/AR207434A1/en active
- 1973-05-28 SE SE7307522A patent/SE415883B/en unknown
- 1973-05-29 GB GB4209675A patent/GB1439512A/en not_active Expired
- 1973-05-29 IL IL42385A patent/IL42385A/en unknown
- 1973-05-29 CA CA172,672A patent/CA985280A/en not_active Expired
- 1973-05-29 GB GB2561373A patent/GB1439511A/en not_active Expired
- 1973-05-30 FI FI1762/73A patent/FI58327C/en active
- 1973-05-31 IN IN1278/CAL/73A patent/IN138966B/en unknown
- 1973-06-04 PH PH14689A patent/PH14204A/en unknown
- 1973-06-04 ZA ZA733763A patent/ZA733763B/en unknown
- 1973-06-05 IE IE896/73A patent/IE38058B1/en unknown
- 1973-06-06 HU HUPI476A patent/HU170491B/hu unknown
- 1973-06-06 ES ES415611A patent/ES415611A1/en not_active Expired
- 1973-06-06 HU HUPI384A patent/HU170487B/hu unknown
- 1973-06-06 NL NL7307867.A patent/NL160814C/en not_active IP Right Cessation
- 1973-06-06 NO NO2379/73A patent/NO146538C/en unknown
- 1973-06-06 HU HUPI477A patent/HU170200B/hu unknown
- 1973-06-07 DD DD171393A patent/DD109211A5/xx unknown
- 1973-06-07 AT AT504873A patent/AT340069B/en not_active IP Right Cessation
- 1973-06-07 JP JP6435173A patent/JPS5715591B2/ja not_active Expired
- 1973-06-07 DE DE2329092A patent/DE2329092A1/en not_active Ceased
- 1973-06-07 BE BE1005125A patent/BE800580A/en not_active IP Right Cessation
- 1973-06-07 CH CH1535876A patent/CH591511A5/xx not_active IP Right Cessation
- 1973-06-07 CH CH831273A patent/CH593929A5/xx not_active IP Right Cessation
- 1973-06-07 FR FR7320753A patent/FR2187344B1/fr not_active Expired
- 1973-06-07 CH CH1535976A patent/CH605887A5/xx not_active IP Right Cessation
- 1973-06-07 CS CS734136A patent/CS200166B2/en unknown
- 1973-06-07 YU YU01526/73A patent/YU36498B/en unknown
- 1973-06-07 LU LU67754A patent/LU67754A1/xx unknown
- 1973-06-07 DD DD180810*A patent/DD115687A5/xx unknown
-
1974
- 1974-03-11 NO NO740850A patent/NO142784C/en unknown
- 1974-09-26 ES ES430416A patent/ES430416A1/en not_active Expired
- 1974-09-26 ES ES430417A patent/ES430417A1/en not_active Expired
-
1975
- 1975-06-06 FR FR7517790A patent/FR2273814A1/en active Granted
- 1975-06-25 PH PH17314A patent/PH13092A/en unknown
-
1976
- 1976-07-19 SE SE7608224A patent/SE418744B/en unknown
- 1976-07-19 SE SE7608225A patent/SE7608225L/en not_active Application Discontinuation
-
1977
- 1977-02-23 IL IL51525A patent/IL51525A0/en unknown
-
1978
- 1978-12-14 NL NL7812163A patent/NL7812163A/en not_active Application Discontinuation
-
1981
- 1981-06-10 JP JP8940881A patent/JPS5731692A/en active Pending
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001058866A2 (en) * | 2000-02-08 | 2001-08-16 | Allergan, Inc. | Ocular hypotensive lipids |
| WO2001058866A3 (en) * | 2000-02-08 | 2002-03-28 | Allergan Sales Inc | Ocular hypotensive lipids |
| US6395787B1 (en) | 2000-02-08 | 2002-05-28 | Allergan Sales, Inc. | Ocular hypotensive lipids |
| WO2002100388A2 (en) * | 2001-06-13 | 2002-12-19 | Allergan, Inc. | Cyclopentane heptan (ene) acyl sulfonamide, 2-alkyl or 2-arylalkyl, or 2-heteroarylalkenyl derivatives as therapeutic agents for the treatment of ocular hypertension |
| WO2002100388A3 (en) * | 2001-06-13 | 2003-11-27 | Allergan Inc | Cyclopentane heptan (ene) acyl sulfonamide, 2-alkyl or 2-arylalkyl, or 2-heteroarylalkenyl derivatives as therapeutic agents for the treatment of ocular hypertension |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |