GB1396206A - Prostaglandins and the preparation thereof - Google Patents
Prostaglandins and the preparation thereofInfo
- Publication number
- GB1396206A GB1396206A GB1542473A GB1542473A GB1396206A GB 1396206 A GB1396206 A GB 1396206A GB 1542473 A GB1542473 A GB 1542473A GB 1542473 A GB1542473 A GB 1542473A GB 1396206 A GB1396206 A GB 1396206A
- Authority
- GB
- United Kingdom
- Prior art keywords
- analogues
- pge
- pgf
- prostaglandins
- 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
- 229940094443 oxytocics prostaglandins Drugs 0.000 title abstract 5
- 150000003180 prostaglandins Chemical class 0.000 title abstract 5
- 239000002253 acid Substances 0.000 abstract 3
- HUHXLHLWASNVDB-UHFFFAOYSA-N 2-(oxan-2-yloxy)oxane Chemical class O1CCCCC1OC1OCCCC1 HUHXLHLWASNVDB-UHFFFAOYSA-N 0.000 abstract 2
- -1 2-tetrahydropyranyl Chemical group 0.000 abstract 2
- 150000007513 acids Chemical class 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 230000003301 hydrolyzing effect Effects 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 abstract 2
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 abstract 1
- DPOINJQWXDTOSF-DODZYUBVSA-N 13,14-Dihydro PGE1 Chemical class CCCCC[C@H](O)CC[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(O)=O DPOINJQWXDTOSF-DODZYUBVSA-N 0.000 abstract 1
- WMHAOJIJVNDMKA-BRIYLRKRSA-N 13,14-Dihydro PGF-1a Chemical compound CCCCC[C@H](O)CC[C@H]1[C@H](O)C[C@H](O)[C@@H]1CCCCCCC(O)=O WMHAOJIJVNDMKA-BRIYLRKRSA-N 0.000 abstract 1
- NVRVNSHHLPQGCU-UHFFFAOYSA-N 6-bromohexanoic acid Chemical compound OC(=O)CCCCCBr NVRVNSHHLPQGCU-UHFFFAOYSA-N 0.000 abstract 1
- IASRMNRQZIRYHM-UHFFFAOYSA-N 6-carboxyhexyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCCCCCC(=O)O)C1=CC=CC=C1 IASRMNRQZIRYHM-UHFFFAOYSA-N 0.000 abstract 1
- JLPQXFFMVVPIRW-UHFFFAOYSA-N 7-bromoheptanoic acid Chemical compound OC(=O)CCCCCCBr JLPQXFFMVVPIRW-UHFFFAOYSA-N 0.000 abstract 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 abstract 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 230000029936 alkylation Effects 0.000 abstract 1
- 238000005804 alkylation reaction Methods 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- HWLZQESIRAGTAT-UHFFFAOYSA-N cyclopenta[b]furan-2-one Chemical class C1=CC2=CC(=O)OC2=C1 HWLZQESIRAGTAT-UHFFFAOYSA-N 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 238000005984 hydrogenation reaction Methods 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 abstract 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 230000000144 pharmacologic effect Effects 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 238000010561 standard procedure Methods 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
- 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 Table
- 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 ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or 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 Table
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Furan Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1396206 Prostaglandins UPJOHN CO 30 March 1973 [27 April 1972] 15424/73 Headings C2C and C2P [Also in Division C3] The invention comprises optically active prostaglandins of the formula or racemates thereof, wherein (a) X is trans- CH=CH- or -CH 2 CH 2 -, and Y is -CH 2 - CH 2 -, or (b) X is trans-CH=CH- and Y is cis-CH=CH-; C n H 2n is C 1-9 alkylene with 1 to 6 carbon atoms in the chain between -CFR 2 - and terminal methyl; g is 2 to 5, M is R 1 is H, C 1-12 alkyl, C 3-10 cycloalkyl, C 7-12 aralkyl, phenyl optionally substituted 1 to 3 times by chlorine atoms or C 1-4 alkyl radicals, R 2 is H, methyl, ethyl or F, and D is one of the four carbocylic radicals the alkanoates thereof wherein the alkanoic acid from which the alkanoate is derived contains 2 to 12 C atoms, and pharmacologically acceptable salts thereof when R 1 is H and their preparation. The PGF 2α analogues are prepared by hydrolysing tetrahydropyranyl ethers of the Formula LI wherein THP is 2-tetrahydropyranyl and M<SP>1</SP> is obtained by the Wittig alkylation with compounds of the formula Hal(CH 2 ) g+1 COOH wherein Hal is Cl or Br, of the appropriate 5α- tetrahydropyran - 2<SP>1</SP> - yloxy - 4# - (3 - tetrahydropyrany - 2<SP>1</SP> - yloxy - 4 - fluoro - 4 - R 2 - trans - 1- alkenyl) - 3,3a#,4,5,6,6a# - hexahydro - 2H- cyclopenta[b]furan-2-ols, which are obtained by reducing the corresponding 2H-cyclopenta[b]- furan-2-ones. The PGE 2 analogues are obtained by oxidizing the tetrahydropyranyl ethers of the Formula LI above and hydrolysing the resulting 9-oxo tetrahydropyranyl ethers. The 13,14-dihydro-PGF 1α and -PGE 1 analogues are made by hydrogenating the corresponding PGF 2α or PGE 2 analogues or the PGF 1α or PGE 1 analogues, which are obtained by the selective hydrogenation of the appropriate PGF 2α and PGE 2 analogues. PGF # analogues are made by reducing the corresponding PGE compounds and separating the mixture of isomers produced. PGA- and PGB-analogues are prepared by treating the corresponding PGE compound with acids and bases respectively. Acids obtained by the above processes may be converted to ester alkanoates and salts by standard methods. 5 - Carboxypentyltriphenylphosponium bromide and 6 - carboxyhexyltriphenylphosphonium bromide are obtained by reacting triphenylphosphine with 6-bromohexanoic acid and 7- bromoheptanoic acid respectively. Pharmaceutical compositions, suitable for oral, parenteral, topical, rectal, sublingual, buccal or vaginal administration, contain the above prostaglandins together with pharmaceutically acceptable carriers. The compounds possess pharmacological activities similar to those of naturally occurring prostaglandins.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US24801372A | 1972-04-27 | 1972-04-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1396206A true GB1396206A (en) | 1975-06-04 |
Family
ID=22937288
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1542473A Expired GB1396206A (en) | 1972-04-27 | 1973-03-30 | Prostaglandins and the preparation thereof |
| GB3200874A Expired GB1396207A (en) | 1972-04-27 | 1973-03-30 | Prostaglandin intermediates and the preparation thereof |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3200874A Expired GB1396207A (en) | 1972-04-27 | 1973-03-30 | Prostaglandin intermediates and the preparation thereof |
Country Status (8)
| Country | Link |
|---|---|
| JP (2) | JPS5939426B2 (en) |
| BE (1) | BE798829A (en) |
| CH (1) | CH585198A5 (en) |
| FR (1) | FR2183041B1 (en) |
| GB (2) | GB1396206A (en) |
| HU (1) | HU168570B (en) |
| NL (1) | NL7305817A (en) |
| ZA (1) | ZA732244B (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2146325A (en) * | 1983-09-07 | 1985-04-17 | Erba Farmitalia | 16-Fluoro-16,17-didehydro prostanoids and process for their preparation |
| WO2002094274A1 (en) * | 2001-05-18 | 2002-11-28 | Sucampo Ag | Cathartic composition |
| CN110218776A (en) * | 2019-06-14 | 2019-09-10 | 苏州叠代生物科技有限公司 | PCR oil phase composition and preparation method thereof |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4052446A (en) * | 1973-08-06 | 1977-10-04 | Hoffmann-La Roche Inc. | 11,16-substituted prostaglandins |
| US4017534A (en) * | 1974-06-03 | 1977-04-12 | American Cyanamid Company | 16-Fluoro-11-deoxy-13-dihydro-prostaglandin |
| JPS52145350A (en) * | 1976-05-31 | 1977-12-03 | Hitachi Ltd | Complete fillet welding of tee joint having vvshaped groove |
| JPS5524138A (en) * | 1978-08-11 | 1980-02-21 | Toray Ind Inc | Optically active synthetic intermediate and its preparation |
| DE3469736D1 (en) * | 1983-09-07 | 1988-04-14 | Indiana University Foundation | 12, 16-DIFLUOROPROSTAGLANDIN F2 ALPHA COMPOUNDS |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL32552A (en) * | 1968-07-29 | 1975-07-28 | Upjohn Co | Prostaglandin analogs |
| BR6915068D0 (en) * | 1969-03-14 | 1973-05-24 | Upjohn Co | PROCESS OF PRODUCTION OF RACEMIC DERIVATIVES OF PROSTAGLANDINE |
-
1973
- 1973-03-30 GB GB1542473A patent/GB1396206A/en not_active Expired
- 1973-03-30 GB GB3200874A patent/GB1396207A/en not_active Expired
- 1973-04-02 ZA ZA732244A patent/ZA732244B/en unknown
- 1973-04-09 JP JP48039666A patent/JPS5939426B2/en not_active Expired
- 1973-04-10 CH CH513473A patent/CH585198A5/xx not_active IP Right Cessation
- 1973-04-26 FR FR7315207A patent/FR2183041B1/fr not_active Expired
- 1973-04-26 NL NL7305817A patent/NL7305817A/xx not_active Application Discontinuation
- 1973-04-27 BE BE130507A patent/BE798829A/en not_active IP Right Cessation
- 1973-04-27 HU HUUO90A patent/HU168570B/hu unknown
-
1983
- 1983-10-25 JP JP58198427A patent/JPS5938235B2/en not_active Expired
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2146325A (en) * | 1983-09-07 | 1985-04-17 | Erba Farmitalia | 16-Fluoro-16,17-didehydro prostanoids and process for their preparation |
| WO2002094274A1 (en) * | 2001-05-18 | 2002-11-28 | Sucampo Ag | Cathartic composition |
| US6956056B2 (en) | 2001-05-18 | 2005-10-18 | Sucampo Ag | Method for providing a cathartic effect |
| AU2002307725B2 (en) * | 2001-05-18 | 2008-07-10 | Sucampo Ag | Cathartic composition |
| US7459583B2 (en) | 2001-05-18 | 2008-12-02 | Sucampo Ag | Method for providing a cathartic effect |
| CN110218776A (en) * | 2019-06-14 | 2019-09-10 | 苏州叠代生物科技有限公司 | PCR oil phase composition and preparation method thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| ZA732244B (en) | 1974-03-27 |
| JPS4914458A (en) | 1974-02-07 |
| JPS5993070A (en) | 1984-05-29 |
| JPS5939426B2 (en) | 1984-09-22 |
| BE798829A (en) | 1973-10-29 |
| JPS5938235B2 (en) | 1984-09-14 |
| CH585198A5 (en) | 1977-02-28 |
| NL7305817A (en) | 1973-10-30 |
| FR2183041B1 (en) | 1977-11-10 |
| HU168570B (en) | 1976-05-28 |
| FR2183041A1 (en) | 1973-12-14 |
| GB1396207A (en) | 1975-06-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |
