GB1398291A - Prostaglandin analogues and production thereof - Google Patents
Prostaglandin analogues and production thereofInfo
- Publication number
- GB1398291A GB1398291A GB1970672A GB1970672A GB1398291A GB 1398291 A GB1398291 A GB 1398291A GB 1970672 A GB1970672 A GB 1970672A GB 1970672 A GB1970672 A GB 1970672A GB 1398291 A GB1398291 A GB 1398291A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydroxy
- octenyl
- analogues
- trans
- formulae
- 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
- 229940006138 antiglaucoma drug and miotics prostaglandin analogues Drugs 0.000 title 1
- 229940094443 oxytocics prostaglandins Drugs 0.000 abstract 5
- 150000003180 prostaglandins Chemical class 0.000 abstract 5
- -1 2-tetrahydropyranyl Chemical group 0.000 abstract 3
- 150000002148 esters Chemical class 0.000 abstract 3
- 230000003301 hydrolyzing effect Effects 0.000 abstract 3
- 229920000858 Cyclodextrin Polymers 0.000 abstract 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 abstract 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 abstract 2
- 150000001298 alcohols Chemical class 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 abstract 2
- VEVBZRMVHQZQEC-UHFFFAOYSA-N (4-ethyl-2-methyl-3-oxooctan-2-yl)phosphonic acid Chemical compound CCCCC(CC)C(=O)C(C)(C)P(=O)(O)O VEVBZRMVHQZQEC-UHFFFAOYSA-N 0.000 abstract 1
- DFXYFRLRTGSPPR-UHFFFAOYSA-N 1-diethoxyphosphorylheptan-2-one Chemical class CCCCCC(=O)CP(=O)(OCC)OCC DFXYFRLRTGSPPR-UHFFFAOYSA-N 0.000 abstract 1
- WIYMDOCSCMPUJI-UHFFFAOYSA-N 1-dimethoxyphosphoryl-3,3-dimethylheptan-2-one Chemical compound CCCCC(C)(C)C(=O)CP(=O)(OC)OC WIYMDOCSCMPUJI-UHFFFAOYSA-N 0.000 abstract 1
- RYCSYYMZXSIBJI-UHFFFAOYSA-N 1-dimethoxyphosphoryl-3-methylheptan-2-one Chemical compound CCCCC(C)C(=O)CP(=O)(OC)OC RYCSYYMZXSIBJI-UHFFFAOYSA-N 0.000 abstract 1
- AITHRLYLAMRNSQ-UHFFFAOYSA-N 5-(triphenyl-$l^{5}-phosphanylidene)pentanoic acid Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=CCCCC(=O)O)C1=CC=CC=C1 AITHRLYLAMRNSQ-UHFFFAOYSA-N 0.000 abstract 1
- 101000692460 Bos taurus Prostaglandin F synthase 1 Proteins 0.000 abstract 1
- 101000692466 Bos taurus Prostaglandin F synthase 2 Proteins 0.000 abstract 1
- YXAGIRHBJJLWHW-UHFFFAOYSA-N Ethyl 2-ethylhexanoate Chemical compound CCCCC(CC)C(=O)OCC YXAGIRHBJJLWHW-UHFFFAOYSA-N 0.000 abstract 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 abstract 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 abstract 1
- 239000000969 carrier Substances 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
- 230000000694 effects Effects 0.000 abstract 1
- 238000006266 etherification reaction Methods 0.000 abstract 1
- LFLSVOVPJVCWKQ-UHFFFAOYSA-N ethyl 2-methylhexanoate Chemical compound CCCCC(C)C(=O)OCC LFLSVOVPJVCWKQ-UHFFFAOYSA-N 0.000 abstract 1
- ZDAFYPGTJKATQZ-UHFFFAOYSA-N ethyl 3,3-dimethylhexanoate Chemical compound CCCC(C)(C)CC(=O)OCC ZDAFYPGTJKATQZ-UHFFFAOYSA-N 0.000 abstract 1
- 238000005984 hydrogenation reaction Methods 0.000 abstract 1
- 150000002596 lactones Chemical class 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
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 238000010561 standard procedure Methods 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
-
- 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
- C07C405/0025—Analogues having the carboxyl group in the side-chains replaced by other functional groups containing keto groups
-
- 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
- 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
Abstract
1398291 Prostaglandins; acylmethane phosphonates ONO PHARMACEUTICAL CO Ltd 27 April 1972 [30 April 1971 17 Nov 1971] 10 Dec 1971] 19706/72 Headings C2C and C2P [Also in Division C3] The invention comprises optically active prostaglandins of the formulae IX, X, XI, XII XIII and XIV wherein X 1 is 3-(R or S)-hydroxy-4-(R or S) methyl - trans - 1 - octenyl, 3 - (S) - hydroxy- 4,4 - dimethyl - trans - 1 - octenyl, or 4 - ethyl- 3-(S)-hydroxy-trans-1-octenyl, the esters thereof, salts thereof, the cyclodextrin clathrates thereof and the esters thereof, PG alcohol derivatives thereof, and the dihydro-PG 1 derivatives thereof, and optically active prostaglandins of the Formulae XV and XVII wherein THP is 2-tetrahydropyranyl and X 2 is 4-(R or S)-methyl-3-(R or S)-tetrahydropyran- 2<SP>1</SP> - yloxy - trans - 1 - octenyl, 4,4 - dimethyl - 3- (S) - tetrahydropyran - 2<SP>1</SP> - yloxy - trans - 1- octenyl, or 4-ethyl-3-(S)-tetrahydropyran-21- yloxy-trans-1-octenyl and their preparation The PGA analogues of Formulae XIII and XIV are prepared by dehydrating the corresponding PGE analogues of the Formulae XI and XII, which are made by oxidizing the 9- hydroxy group in compounds of the Formulae XV and XVII and hydrolysing the resulting products. PGF analogues of the Formulae IX and X are prepared by hydrolysing the corresponding PGF analogues of the Formulae XV and XVII. The dihydro-PG 1 analogues are obtained by hydrogenating the corresponding PG 1 analogues. The corresponding ester, alcohols, salts and cyclodextrin clathrates are prepared by standard methods. PGF 1 analogues of the Formula XVII are made by the selective hydrogenation of the corresponding PGF 2 analogues of the Formula XV which are prepared by reacting 4-carboxybutylidenetriphenylphosphorane with cyclopenta[b]p-urans of the formula obtained by reducing the corresponding lactones, resulting from the etherification of the corresponding 5a-hydroxy-4#-X 1 -3,3a#,4,5,6,6a#-hexahydro-2H-cyclopenta[b]-furan-2-ones, which are made by hydrolysing the appropriate 5α- acetoxy - 4# - X 1 - 3,3a#,4,5,6,6a# - hexahydro - 2H - cyclopenta[b]furan - 2 - ones, obtained by reducing the corresponding 5α- acetoxy - 4# - (3 - oxo - octenyl) - 3,3a#,4,5,6,6a#- hexahydro - 2H - cyclopenta[b]furan - 2 - ones, which are prepared by reacting 5α-acetoxy-4#- formyl - 3,3a#,4,5,6,6a# - hexahydro - 2H - cyclopenta[b]furan-2-one with the appropriate dimethyl or diethyl 2-oxoheptylphosphonates. 4α - Hydroxy - 2α - (7 - hydroxy - cis - 2- heptenyl) - 3# - (3 - (S) - hydroxy - 4 - (S)- methyl - trans - 1 - octenyl)cyclopentanone oxime is obtained by reducing 4α-hydroxy-2α-(6- methoxycarbonyl - cis - 2 - hexenyl) - 3# - (3 - (S)- hydroxy - 4 - (S) - methyl - trans-1-octenyl)cyclopentanone oxime, which is prepared by reacting the methyl ester of 16-(S)-methyl-PGE 2 with hydroxylamine hydrochloride. Dimethyl - 2 - oxo - 3 - methylheptylphosphonate, dimethyl - 2 - oxo - 3,3 - dimethylheptylphosphonate and dimethyl-2-oxo-3-ethylheptylphosphonate are prepared by dimethyl methylphosphonate with ethyl 2-methylhexanoate, ethyl 3,3-dimethylhexanoate and ethyl 2-ethylhexanoate respectively in the presence of butyllithium. Pharmaceutical compositions, suitable for oral, parenteral, sublingual, vaginal and rectal administration, contain the prostaglandins of the Formulae IX to XIV or derivatives thereof and suitable carriers. The compounds possess similar activities to those of naturally occurring prostaglandins. Reference has been directed by the Comptroller to Specification 1,198,071.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2909671 | 1971-04-30 | ||
JP9211371A JPS4854068A (en) | 1971-11-17 | 1971-11-17 | |
JP46099936A JPS4864073A (en) | 1971-04-30 | 1971-12-10 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1398291A true GB1398291A (en) | 1975-06-18 |
Family
ID=27286426
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB1970672A Expired GB1398291A (en) | 1971-04-30 | 1972-04-27 | Prostaglandin analogues and production thereof |
GB38475A Expired GB1398838A (en) | 1971-04-30 | 1972-04-27 | Prostaglandin analogues and production thereof |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB38475A Expired GB1398838A (en) | 1971-04-30 | 1972-04-27 | Prostaglandin analogues and production thereof |
Country Status (12)
Country | Link |
---|---|
JP (1) | JPS4864073A (en) |
AR (1) | AR196490A1 (en) |
BE (1) | BE782822A (en) |
CA (1) | CA988083A (en) |
CH (1) | CH575368A5 (en) |
DD (1) | DD99563A5 (en) |
DE (1) | DE2221301A1 (en) |
ES (1) | ES402263A1 (en) |
GB (2) | GB1398291A (en) |
HU (1) | HU168838B (en) |
NL (1) | NL7205806A (en) |
SE (1) | SE7507619L (en) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS4949963A (en) * | 1972-09-16 | 1974-05-15 | ||
US3962312A (en) * | 1972-09-21 | 1976-06-08 | Ono Pharmaceutical Company | 9,11,15-Trihydroxy prost-5-enoic acid analogues |
IL50310A (en) * | 1972-11-08 | 1977-08-31 | Pfizer | Dimethyl ketophosphonates |
JPS5720305B2 (en) * | 1973-02-28 | 1982-04-27 | ||
JPS5823393B2 (en) * | 1974-03-14 | 1983-05-14 | オノヤクヒンコウギヨウ カブシキガイシヤ | prostaglandin |
-
1971
- 1971-12-10 JP JP46099936A patent/JPS4864073A/ja active Pending
-
1972
- 1972-04-27 GB GB1970672A patent/GB1398291A/en not_active Expired
- 1972-04-27 GB GB38475A patent/GB1398838A/en not_active Expired
- 1972-04-28 NL NL7205806A patent/NL7205806A/xx not_active Application Discontinuation
- 1972-04-28 AR AR241703A patent/AR196490A1/en active
- 1972-04-28 BE BE782822A patent/BE782822A/en unknown
- 1972-04-28 CH CH636272A patent/CH575368A5/xx not_active IP Right Cessation
- 1972-04-29 DE DE19722221301 patent/DE2221301A1/en active Pending
- 1972-04-29 HU HUOO180A patent/HU168838B/hu unknown
- 1972-04-29 ES ES402263A patent/ES402263A1/en not_active Expired
- 1972-05-01 CA CA141,153A patent/CA988083A/en not_active Expired
- 1972-05-02 DD DD162679A patent/DD99563A5/xx unknown
-
1975
- 1975-07-02 SE SE7507619A patent/SE7507619L/en unknown
Also Published As
Publication number | Publication date |
---|---|
NL7205806A (en) | 1972-11-01 |
CH575368A5 (en) | 1976-05-14 |
CA988083A (en) | 1976-04-27 |
ES402263A1 (en) | 1976-01-01 |
DD99563A5 (en) | 1973-08-12 |
AR196490A1 (en) | 1974-02-06 |
JPS4864073A (en) | 1973-09-05 |
GB1398838A (en) | 1975-06-25 |
HU168838B (en) | 1976-07-28 |
BE782822A (en) | 1972-08-16 |
SE7507619L (en) | 1975-07-02 |
DE2221301A1 (en) | 1972-11-23 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PS | Patent sealed | ||
433D | Application made for revocation (sect. 33/1949) | ||
433C | Case decided by the comptroller ** specification amended (sect. 33/1949) | ||
SPA | Amended specification published | ||
PCNP | Patent ceased through non-payment of renewal fee |