GB1476661A - Prostaglandins - Google Patents

Prostaglandins

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Publication number
GB1476661A
GB1476661A GB2113274A GB2113274A GB1476661A GB 1476661 A GB1476661 A GB 1476661A GB 2113274 A GB2113274 A GB 2113274A GB 2113274 A GB2113274 A GB 2113274A GB 1476661 A GB1476661 A GB 1476661A
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United Kingdom
Prior art keywords
formula
alkyl
compounds
optionally
substituted
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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
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GB2113274A
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Wyeth Holdings LLC
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American Cyanamid Co
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Publication date
Application filed by American Cyanamid Co filed Critical American Cyanamid Co
Priority to GB2113274A priority Critical patent/GB1476661A/en
Priority to AU69162/74A priority patent/AU493932B2/en
Priority to DE19742425573 priority patent/DE2425573A1/en
Priority to FR7418287A priority patent/FR2272641B1/fr
Priority to BE145128A priority patent/BE815979A/en
Publication of GB1476661A publication Critical patent/GB1476661A/en
Expired legal-status Critical Current

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    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/38—Compounds containing oxirane rings with hydrocarbon 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
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    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
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    • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
    • C07C29/143—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of ketones
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    • C07C29/32—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions without formation of -OH groups
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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    • C07C31/13—Monohydroxylic alcohols containing saturated rings
    • C07C31/133—Monohydroxylic alcohols containing saturated rings monocyclic
    • C07C31/1333—Monohydroxylic alcohols containing saturated rings monocyclic with a three-membered ring
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    • C07C33/40—Halogenated unsaturated alcohols
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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    • C07—ORGANIC CHEMISTRY
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    • 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
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    • 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
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    • 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
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Abstract

1476661 Prostaglandins AMERICAN CYANAMID CO 13 May 1974 21132/74 Headings C2C C2J and C2P [Also in Division C3] The invention comprises prostaglandins of the Formulae A and B wherein the side chains attached to the C 8 and C 12 positions of the cyclopentane, cyclopentene or cyclohexane ring are trans to each other and a hydroxy substituent at the C 11 position is trans to the side chain at the C 12 position; Y is Z is -(CH 2 ) m -, -(CH 2 ) m -C(R 4 ) 2 -CH 2 -, -(CH 2 ) m -CH(R 5 )-, -(CH 2 ) m -O-CH 2 -, cis-CH 2 -CH=CH-CH(R 6 )-(CH 2 ) p - or -(CH 2 ) m -S-CH 2 -, wherein m is 3 to 8, p is 1 to 5, R 4 is C 1-3 alkyl, R 5 is C 1-3 alkyl, F or phenyl, and R 6 is H or C 1-4 alkyl; -C 13 -C 14 - is ethylene or trans-vinylene; R 1 is C 1-3 alkyl; X is -CH 2 -, -CH 2 CH 2 - or Q is wherein R 7 is H or C 1-3 alkyl; R 3 is OH, C 1-12 alkoxy, 2-tetrahydropyranyloxy or trialkylsilyloxy; s is 0 to 5; t is 0 or 1; and R is C 5-9 cycloalkyl, C 5-9 cycloalkenyl, mono- or dialkyl substituted C 3-8 cyclo-alkyl or mono- or di-alkyl substituted C 5-8 cycloalkenyl; with the first proviso that when s and t are both 0 and -C 13 -C 14 - is trans-vinylene then R cannot be an optionally substituted cyclopropyl group; with the second proviso that when Z is -(CH 2 ) m - or and R is optionally substituted cycloalkyl then the sum of s and t is at least 1; and with the third proviso that when -C 13 -C 14 - is ethylene then Z cannot be and pharmaceutically acceptable salts thereof when R 3 is OH. The compounds are prepared by reacting cyclopentenones or cyclohexenones of the Formula H and R<SP>1</SP> 3 has all the values of R 3 except hydroxy, with alonates of the formula where R 9 is alkyl and R<SP>1</SP> 2 is triphenylmethyl or mono- or di-methoxy-substituted triphenylmethyl, to give compounds of the Formula J followed by hydrolysing the ester and ester groups with weak acids, to give compounds of the Formula K wherein R<SP>11</SP> 3 is OH or C 1-12 alkoxy, and optionally hydrolysing those compounds in which R 3 <SP>11</SP> is C 1-12 alkoxy; optionally hydrogenating the C 13 -C 44 double bonds; optionally dehydrating the resulting compounds in which X is to give compounds of the Formula B above, optionally reducing the 9-oxo groups, and optionally introducing a C 1-3 alkyl group at C 16 in a known manner. The following intermediates and starting materials were also prepared: cyclopentenones or cyclohexenones of Formula H above including compounds in which X<SP>1</SP> is 2 - (# - carboxy - 2 - cis - alkenyl) - 3,4 - epoxycyclopentanol; 2 - (# - carboxy - 2 - cis - alkenyl) - 3,4 - epoxycyclopentanone; alkenes of the formula wherein R<SP>11</SP> 2 is H, triphenylmethoxy or mono- or di-methoxy substituted triphenylmethoxy; methyl and ethyl 2-(2-methoxyethyl)-2-oxocyclopentanecarboxylates; 2 - (2 - methoxyethyl)cyclopentan - 1 - one; 1 - acetoxy - 2- (2 - methoxyethyl)cyclopent - 1 - ene; 2 - (2- hydroxyethyl) - 2 - cyclopenten - 1 - one; 2- formyl - methyl - 2 - cyclpenten - 1 - one; 2- oxa - 3 - hydroxybicyclo[3,3,0]oct - 6 - ene; 2 - bromo - 2 - (2 - methoxyethyl)cyclopentan- 1 - one; 2 - (# - carboxy - 2 - cis - alkenyl) - 3- cyclopenten - 1 - ols; 2 - (# - carboxy - 2 - cisalkenyl) - 3 - cyclpenten - 1 - ones; compounds of the Formula A above in which R 3 is OCH 3 , Y is and Q is Phosphonium bromides of the formula wherein A is C 3-7 alkylene, are prepared by reacting phosphine with the acids of the formula BrACOOH. Alanates of the formula wherein R 9 is alkyl and R<SP>1</SP> 2 is triphenylmethyl or mono- or di-methoxy substituted triphenylmethyl are prepared by reacting trialkyl aluminiums with (3-OR<SP>1</SP> 2 -1-trans-alkenyl) lithiums of the formula obtained by reacting the corresponding S-OR<SP>1</SP> 2 - 1-halo-1-trams-alkenes with butyl lithium. Pharmaceutical compositions, suitable for oral or parenteral administration, contain the above prostaglandins and pharmaceutically acceptable carriers or diluents. The compounds are used as hypotensive agents.
GB2113274A 1974-05-13 1974-05-13 Prostaglandins Expired GB1476661A (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
GB2113274A GB1476661A (en) 1974-05-13 1974-05-13 Prostaglandins
AU69162/74A AU493932B2 (en) 1974-05-13 1974-05-20 Novel prostaglandins
DE19742425573 DE2425573A1 (en) 1974-05-13 1974-05-27 NEW PROSTAGLANDIN
FR7418287A FR2272641B1 (en) 1974-05-13 1974-05-27
BE145128A BE815979A (en) 1974-05-13 1974-06-06 NEW 15-HYDROXYPROSTANOIC ACID DERIVATIVES AND THEIR PROCESS FOR PREPARATION.

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
GB2113274A GB1476661A (en) 1974-05-13 1974-05-13 Prostaglandins
AU69162/74A AU493932B2 (en) 1974-05-13 1974-05-20 Novel prostaglandins
DE19742425573 DE2425573A1 (en) 1974-05-13 1974-05-27 NEW PROSTAGLANDIN
FR7418287A FR2272641B1 (en) 1974-05-13 1974-05-27
BE145128A BE815979A (en) 1974-05-13 1974-06-06 NEW 15-HYDROXYPROSTANOIC ACID DERIVATIVES AND THEIR PROCESS FOR PREPARATION.

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GB1476661A true GB1476661A (en) 1977-06-16

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GB2113274A Expired GB1476661A (en) 1974-05-13 1974-05-13 Prostaglandins

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AU (1) AU493932B2 (en)
BE (1) BE815979A (en)
DE (1) DE2425573A1 (en)
FR (1) FR2272641B1 (en)
GB (1) GB1476661A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5185374A (en) * 1988-05-11 1993-02-09 K.K. Ueno Seiyaku Oyo Kenkyujo Use of 15-ketoprostaglandin E or F compounds for uterine contraction

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4074063A (en) * 1976-02-11 1978-02-14 Miles Laboratories, Inc. Bicycloalkyl derivatives of prostaglandins
CA1322749C (en) * 1987-01-28 1993-10-05 Ryuzo Ueno Prostaglandins of the d series, and tranquilizers and soporifics containing the same
CA1323364C (en) * 1987-01-28 1993-10-19 Ryuzo Ueno Prostaglandins e and anti ulcer agents containing same
CA1324129C (en) * 1987-04-30 1993-11-09 Ryuzo Ueno Prostaglandins of the f series
DE3876050T2 (en) * 1987-09-18 1993-03-25 R Tech Ueno Ltd OCULAR HYPOTENSIVAGENTS.

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5185374A (en) * 1988-05-11 1993-02-09 K.K. Ueno Seiyaku Oyo Kenkyujo Use of 15-ketoprostaglandin E or F compounds for uterine contraction

Also Published As

Publication number Publication date
BE815979A (en) 1974-12-06
FR2272641B1 (en) 1978-02-03
AU6916274A (en) 1975-11-20
FR2272641A1 (en) 1975-12-26
AU493932B2 (en) 1975-11-20
DE2425573A1 (en) 1975-12-11

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