GB1377258A - Derivatives of 9-oxo-13-trans-prostenoic acid esters - Google Patents

Derivatives of 9-oxo-13-trans-prostenoic acid esters

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Publication number
GB1377258A
GB1377258A GB3199672A GB3199672A GB1377258A GB 1377258 A GB1377258 A GB 1377258A GB 3199672 A GB3199672 A GB 3199672A GB 3199672 A GB3199672 A GB 3199672A GB 1377258 A GB1377258 A GB 1377258A
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alkyl
formula
ethoxycarbonylalkyl
straight chain
compounds
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GB3199672A
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Wyeth Holdings LLC
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American Cyanamid Co
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Publication of GB1377258A publication Critical patent/GB1377258A/en
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/36—Radicals substituted by singly-bound nitrogen atoms
    • C07D213/40—Acylated substituent nitrogen atom
    • 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
    • C07C405/0016—Analogues having the carboxyl group in the side-chains replaced by other functional groups containing only hydroxy, etherified or esterified hydroxy groups
    • 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
    • C07C405/0025—Analogues having the carboxyl group in the side-chains replaced by other functional groups containing keto groups
    • 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
    • C—CHEMISTRY; METALLURGY
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    • 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
    • C07C405/005—Analogues or derivatives having the five membered ring replaced by other rings
    • C07C405/0058—Analogues or derivatives having the five membered ring replaced by other rings having the side-chains or their analogues or derivatives attached to a not condensed ring different from a five-membered ring
    • C07C405/0066—Analogues or derivatives having the five membered ring replaced by other rings having the side-chains or their analogues or derivatives attached to a not condensed ring different from a five-membered ring to a six-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
    • C07C51/377—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
    • C07C51/38—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups by decarboxylation
    • C—CHEMISTRY; METALLURGY
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/58—Preparation of carboxylic acid halides
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
    • C07C53/15—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen containing halogen
    • C07C53/19—Acids containing three or more carbon atoms
    • C—CHEMISTRY; METALLURGY
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/01—Saturated compounds having only one carboxyl group and containing hydroxy or O-metal groups
    • C—CHEMISTRY; METALLURGY
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    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/185—Saturated compounds having only one carboxyl group and containing keto groups
    • C07C59/205—Saturated compounds having only one carboxyl group and containing keto groups containing rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/76—Unsaturated compounds containing keto groups
    • C07C59/80—Unsaturated compounds containing keto groups containing rings other than six-membered aromatic rings
    • C07C59/82—Unsaturated compounds containing keto groups containing rings other than six-membered aromatic rings the keto group being part of a ring
    • C—CHEMISTRY; METALLURGY
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D207/20—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen 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
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/65—One oxygen atom attached in position 3 or 5
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen 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
    • C07D213/72—Nitrogen atoms
    • C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
    • C07D221/20—Spiro-condensed ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
    • C07D295/182—Radicals derived from carboxylic acids
    • C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
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    • 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
    • C07D317/72—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 spiro-condensed with carbocyclic rings

Abstract

1377258 Prostaglandins AMERICAN CYANIMID CO 7 July 1972 [14 July 1971 (2) 16 Dec 1971] 31996/72 Heading C2C [Also in Division C5] The invention comprises prostaglandins of the formula wherein n is 1 or 2; Y is R 1 is a straight chain C 3-10 alkyl, a straight chain C 2-6 alkyl having one branched CH 3 group, a straight chain C 3-6 alkenyl, a straight chain C 3-6 -#-haloalkyl, a straight chain C 3-6 -#-mercaptoalkyl, a straight chain C 4-7 -#-carboxyalkyl or a radical of the formulµ wherein p is 2 to 4, q is 3 to 6, R 3 is C 1-3 alkyl, R 4 and R 5 each are H or C 1-4 alkyl or R 4 and R 5 , together with the N atom to which they are attached, form a 1-pyrrolidinyl, piperidino or morpholino group; R 2 is OH, C 1-4 alkoxy, pyridyloxy, 2,2,2-trichloroethoxy, wherein R 6 is H, C 1-4 alkyl, C 2-4 alkenyl, C 2-4 alkynyl, cyclohexyl, phenyl-C 1-4 alkyl, or C 1-4 - #-hydroxyalkyl, and R 7 is H, C 1-4 alkyl, OH, C 2-4 alkenyl, C 2-4 alkynyl, cyclohexyl, phenyl, trifluoromethylphenyl, di - (C 1-4 alkyl) aminophenyl, chlorophenyl, C 1-4 alkylphenyl, pyridyl, phenyl-C 1-4 alkyl, pyridyl-C 1-4 alkyl, C 1-4 #- hydroxyalkyl, #-C 1-4 alkoxy-C 1-4 alkyl, #-di- (C 1-4 alkyl)amino-C 1-4 alkyl, #-piperidino-C 1-4 - alkyl, #-(1-pyrrohdinyl)-C 1-4 alkyl, #-morpholino-C 1-4 alkyl, NH 2 , di-(C 1-4 alkyl)amino, piperidino, hexamethyleneimino morpholino, anilino, or 4-(C 1-4 alkyl)-1-piperazinyl, or R 6 and R 7 , taken together with the N atom to which they are attached, form a 1-pyrrolidinyl, morpholino, hexamethyleneimino, 4 - phenylpiperidino, 4- (C 1-4 alkyl) - 1 - piperazinyl, 4 - phenyl - 1- piperazinyl, 3 - pyrrolin - 1 - yl, 1,2,5,6 - tetrahydro - 1 - pyridyl, 3 - azabicyclo[3,2,2]non- 3 - yl, N,N<SP>1</SP> - bis - di - (C 1-4 alkyl)aminophenylureido or 3 - azaspiro[5,5]undec - 3 - yl; and Z is a radical of the formula cis wherein m is 1 to 8, with the provisos that (i) when R 2 is N(R 6 )R 7 , then R 1 is a straight chain C 3-10 alkyl, a straight chain C 2-6 alkyl having one branched CH 3 , a straight chain C 3-6 alkenyl straight chain #-halo-C 3-6 alkyl or a radical of the formulµ (ii) when R 1 is #-carboxyalkyl then R 2 is OH, and (iii) when R 1 is -(CH 2 ) p -CH-(COOR 3 ) 2 then R 2 is C 1-4 alkoxy, pharmaceutically acceptable acid addition salts of the compounds of the above formula which possess basic nitrogen atoms and salts of the compounds of the above formula when R 1 is #-carboxyalkyl and/ or R 2 is H with pharmaceutioally acceptable cations. The compounds are prepared by reacting cyclopentenones of the Formula II: wherein R<SP>1</SP> is alkyl and Z<SP>1</SP> is with reagents of the formula wherein R<SP>11</SP> is C 1-6 alkyl and R is C 3-10 alkyl, C 2-4 alkyl having one branched CH 3 , C 3-6 alkenyl or C 3-6 -#-chloroalkyl, in inert solvents and hydrolysing the resulting adducts, and, if desired, when Z<SP>1</SP> is -CH 2 - in the resulting product of the Formula IV: converting 2<SP>1</SP> to CH 2 CH = CH(CH 2 ) p by reacting compound of Formula IV with ethylene glycol, reducing the resulting 9.9-ethylenedioxy compounds, treating the aldehydes thus obtained with reagents of the formula and hydrolysis the resulting compounds; and, if desired, converting the compounds of Formula IV above wherein 2<SP>1</SP> is replaced by 2 and wherein R is #-chloroalkyl into compound in which R is #-fluoro-, bromo- or iodo-alkyl, #- carboxyalkyl, (CH 2 ) p S-R 3 , -(CH 2 ) p S(O)R 3 , (CH 2 ) p OR 3 , -(CH 2 ) p -CH(CO 2 R 3 ) 2 or (CH 2 ) q - N(R 4 )R 5 by standard methods, and, if desired, hydrolysing the esters to the corresponding acids, and re-esterifying the resulting acids; converting them to amides of the invention via the formation of the corresponding acid chlorides and if desired reducing the 9-oxo group to the 9-hydroxy group. The following intermediates are also prepared: 4 - chloro - 1 - tetrahydropyran - 2<SP>1 </SP>- yloxybutane, diethyl - (1,1 - dimethyl - 5 - tetrahydropyran - 2<SP>1 </SP>- yloxypentyl) - malonate, diethyl (1,1 - dimethyl - 5 - hydroxypentyl)- malonate, 3,3 - dimethyl - 7 - hydroxyheptanoic acid, 3,3 - dimethyl - 7 - chloroheptanoic acid and its ethyl ester, ethyl 3,3-dimethyl-7-iodoheptanoate, diethyl - (5 - chloro - 1,1 - dimethyl) pentyl)malonate, methyl and ethyl 1-(#-ethoxycarbonylalkyl) - 2 - oxocyclopentanecarboxylate, methyl and ethyl 1-( #-ethoxycarbonylalkyl) - 2 - oxacyclohexanecarboxylate, 2 - (#- carboxyalkyl) cyclopentan-1-one, 2-(#-carboxyalkyl) cyclohexan - 2 - one, 2 - (# - ethoxycarbonylalkyl) cyclopentan - 2 - one, 2 - (#- ethoxycarbonylalkyl) cyclopentan - 2 - one, 1- acetoxy - 2 - (# - ethoxycarbonylalkyl) cyclopent - 1 - ene, 1 - acetoxy - 2 - (# - ethoxycarbonylalkyl) cyclohex - 1 - ene, 2 - bromo - 2- (# - ethoxycarbonylalkyl) cyclopentan - 1 - one, 2 - bromo - 2 - (# - ethoxycarbonylalkyl) cyclohexan - 1 - one, 1 - methoxyimino - 2 - (# - ethoxycarbonylalkyl) - 2 - cyclopentene, 1 - methoxyimino - 2 - (# - ethoxycarbonylalkyl)- 2- cyclohexene, 1 - methoxyimino - 2 - (# - hydroxyalkyl) - 2 - cyclopentene and 1 - methoxyimino - 2 - (# - hydroxyalkyl) - 2 - cyclohexene, and the p-toluenesulphonates thereof, 1-methoxyimino - 2 - (#,# - diethoxycarbonylalkyl)- 2-cyclopentene (or cyclohexene), 1-methoxyimino - 2 - (#,# - dicarboxyalkyl) - 2 - cyclopentene (or cyclohexene, 1-methoxyimino-2-(#- carboxyalkyl) - 2 - cyclopentene (or cyclohexene), compounds of the above Formula I in which Y is -OCH 2 CH 2 O-, R 1 is #-iodoalkyl, -(CH 2 ) p OR 3 , -(CH 2 ) q N(R 4 )R 5 , #-phthalimidoalkyl, R 2 is ethoxy and 2 is (CH 2 ) m , and compounds of the Formula II above. Pharmaceutical compositions contain the above prostaglandins and pharmaceutically acceptable carriers or diluents. The compounds possess hypotensive, antimicrobial, antifungal and anti-inflammatory, activities. They also inhibit the secretion of gastric acid, provide protection against the ulcerogenic properties of indomethacin, and possess activity as fertility controlling agents, central nervous system regulatory agents, salt-and water-retention regulatory agents, fat metabolic regulatory agents, serum chlolesterol-lowering agents and as abortifacients, anticonvulsants, and bronchodilators.
GB3199672A 1971-07-14 1972-06-07 Derivatives of 9-oxo-13-trans-prostenoic acid esters Expired GB1377258A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US16271171A 1971-07-14 1971-07-14
US16271271A 1971-07-14 1971-07-14
US20895171A 1971-12-16 1971-12-16

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GB1377258A true GB1377258A (en) 1974-12-11

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AR (2) AR193266A1 (en)
BE (1) BE786215A (en)
CA (1) CA987314A (en)
CH (1) CH576419A5 (en)
DE (1) DE2234706A1 (en)
ES (1) ES404882A1 (en)
GB (1) GB1377258A (en)
IL (1) IL39481A (en)
NL (1) NL7208576A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8202909B2 (en) 2005-01-27 2012-06-19 Sucampo Ag Method for treating central nervous system disorders

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* Cited by examiner, † Cited by third party
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US4044043A (en) * 1973-12-26 1977-08-23 American Cyanamid Company Derivatives of 9-oxo-13-trans-prostenoic acid esters
CA1148149A (en) 1977-12-08 1983-06-14 Allan Wissner Prostaglandin activity

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8202909B2 (en) 2005-01-27 2012-06-19 Sucampo Ag Method for treating central nervous system disorders

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IL39481A0 (en) 1972-07-26
DE2234706A1 (en) 1973-02-01
AR193266A1 (en) 1973-04-11
AR203717A1 (en) 1975-10-15
CA987314A (en) 1976-04-13
CH576419A5 (en) 1976-06-15
BE786215A (en) 1973-01-15
NL7208576A (en) 1973-01-16
ES404882A1 (en) 1976-01-01
IL39481A (en) 1975-07-28

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PS Patent sealed [section 19, patents act 1949]
PCNP Patent ceased through non-payment of renewal fee