GB1282661A - Prostaglandins and the manufacture thereof - Google Patents
Prostaglandins and the manufacture thereofInfo
- Publication number
- GB1282661A GB1282661A GB01510/70A GB1151070A GB1282661A GB 1282661 A GB1282661 A GB 1282661A GB 01510/70 A GB01510/70 A GB 01510/70A GB 1151070 A GB1151070 A GB 1151070A GB 1282661 A GB1282661 A GB 1282661A
- Authority
- GB
- United Kingdom
- Prior art keywords
- racemic
- derivatives
- pge
- alkyl
- atoms
- 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 3
- 150000003180 prostaglandins Chemical class 0.000 title abstract 3
- 238000004519 manufacturing process Methods 0.000 title 1
- 239000002253 acid Substances 0.000 abstract 5
- 125000000217 alkyl group Chemical group 0.000 abstract 5
- 101000692466 Bos taurus Prostaglandin F synthase 2 Proteins 0.000 abstract 4
- 150000002148 esters Chemical class 0.000 abstract 4
- 150000003166 prostaglandin E2 derivatives Chemical class 0.000 abstract 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 4
- 150000007513 acids Chemical class 0.000 abstract 3
- 229910052799 carbon Inorganic materials 0.000 abstract 3
- 150000003155 prostaglandin A2 derivatives Chemical class 0.000 abstract 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 abstract 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 2
- 229910052794 bromium Inorganic materials 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 229910052801 chlorine Inorganic materials 0.000 abstract 2
- 239000000460 chlorine Substances 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 125000001153 fluoro group Chemical group F* 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- 150000003158 prostaglandin B2 derivatives Chemical class 0.000 abstract 2
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 abstract 1
- 108700023418 Amidases Proteins 0.000 abstract 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 abstract 1
- 230000002378 acidificating effect Effects 0.000 abstract 1
- 125000005907 alkyl ester group Chemical group 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 102000005922 amidase Human genes 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 1
- 239000000969 carrier Substances 0.000 abstract 1
- 239000003638 chemical reducing agent Substances 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- 230000018044 dehydration Effects 0.000 abstract 1
- 238000006297 dehydration reaction Methods 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 125000004185 ester group Chemical group 0.000 abstract 1
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical group C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 244000005700 microbiome Species 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 238000007911 parenteral administration Methods 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 238000011200 topical administration Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C35/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C35/22—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system
- C07C35/23—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system with hydroxy on a condensed ring system having two rings
- C07C35/27—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system with hydroxy on a condensed ring system having two rings the condensed ring system containing six carbon atoms
-
- 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
- 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
- C07D317/10—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 not condensed with other rings
- C07D317/14—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 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/26—Radicals substituted by doubly bound oxygen or sulfur atoms or by two such atoms singly bound to the same carbon atom
-
- 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
- C07D317/10—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 not condensed with other rings
- C07D317/14—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 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/30—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
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P31/00—Preparation of compounds containing a five-membered ring having two side-chains in ortho position to each other, and having at least one oxygen atom directly bound to the ring in ortho position to one of the side-chains, one side-chain containing, not directly bound 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 at least one oxygen atom bound in gamma-position to the ring, e.g. prostaglandins
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Biotechnology (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
1282661 Prostaglandins UPJOHN CO 10 March 1970 [14 March 1969] 11510/70 Heading C2C The invention comprises novel racemic prostaglandins of the formulµ wherein R 1 is H, C 1-8 alkyl, C 3-10 cycloalkyl, C 7-12 aralkyl, phenyl, phenyl substituted with 1 to 3 chlorine atoms or C 1-4 alkyl, or ethyl substituted in the beta position with 3 chlorine, 2 or 3 bromine or 1, 2 or 3 iodine atoms; R 2 is H or C 1-10 alkyl, optionally substituted with 1 to 3 F atoms; R 3 and R 4 are H or C 1-4 alkyl; A is C 1-10 alkylene, optionally substituted with 1 or 2 F atoms, and with 1 to 5 C atoms between COOR 1 and V; V is cis-CH=CH- or -C#C-; and #indicates attachment of the group to the ring in alpha or beta configuration, pharmacologically acceptable salts thereof when R 1 is H, excepting racemic PGE 2 and racemic PGF 2 α, and the preparation of the above novel racemic compounds and racemic PGE 2 and racemic PGF 2 α. Racemic PGE 2 derivatives of the Formula XLII wherein R 1 is other than H are prepared by reacting the oxo or endo forms of disulphonic acid esters of the formula wherein R 14 is the same as R 1 except R 14 does not include H and R 15 is C 1-5 alkyl with water at temperatures in the range of 0 to 60 C. Racemic PGA 2 derivatives of the above Formula XLI, wherein R 1 is other than H are obtained either by reacting the above disulphonic acid esters at temperatures in the range of 40 to 100 C. with combinations of water, bases characterized by their water solutions having pH's 8 to 12, and sufficient inert watersoluble organic diluents to form basic and substantially homogeneous reaction mixtures or by the acidic dehydration of the corresponding racemic PGE 2 derivatives. Racemic PGF 2 derivatives of the Formula XLIII above are prepared reacting the corresponding PGE 2 derivatives with carbonyl reducing agents which do not affect ester groups or ethylenic or acetylenic linkages. Racemic PGB 2 derivatives of the above Formula XL are made reacting the corresponding PGE 2 or PGA2 derivatives with bases whose water solutions have pH's greater than 10. The free acids of the above racemic PGE 2 , PGF 2 , PGA 2 and PGB 2 derivatives form the corresponding alkyl esters by subjecting the said esters to the acylase enzyme systems of microorganism species of Subphylum 2 of Phylum 111. Esters of the above Formulae XL, XLI, XLII and XLIII in which R 1 is an ethyl radical substituted in the beta position by 3 chlorine, 2 or 3 bromine, or 1, 2 or 3 iodine atoms are converted to the corresponding free acids by treatment with zinc dust and alkanoic acids with 2 to 6 carbon atoms. Pharmaceutical compositions, having prosta. glandin-like activity, contain the above novel compounds and pharmaceutical acceptable carriers. The compositions may be in forms suitable for oral, parenteral or topical administration.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US80740569A | 1969-03-14 | 1969-03-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1282661A true GB1282661A (en) | 1972-07-19 |
Family
ID=25196294
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB01510/70A Expired GB1282661A (en) | 1969-03-14 | 1970-03-10 | Prostaglandins and the manufacture thereof |
| GB58026/71A Expired GB1282662A (en) | 1969-03-14 | 1970-03-10 | Bicyclo[3,1,0]hexan-3-one derivatives and the manufacture thereof |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB58026/71A Expired GB1282662A (en) | 1969-03-14 | 1970-03-10 | Bicyclo[3,1,0]hexan-3-one derivatives and the manufacture thereof |
Country Status (10)
| Country | Link |
|---|---|
| BE (1) | BE747348A (en) |
| BR (1) | BR6915068D0 (en) |
| CA (1) | CA968348A (en) |
| CH (3) | CH549549A (en) |
| DE (1) | DE2011969A1 (en) |
| ES (1) | ES377342A1 (en) |
| FR (1) | FR2034951B1 (en) |
| GB (2) | GB1282661A (en) |
| IL (1) | IL33949A (en) |
| NL (1) | NL7003298A (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4001300A (en) * | 1975-02-24 | 1977-01-04 | The Upjohn Company | 2,2-Difluoro-16-phenoxy-PGF2 analogs |
| US4056555A (en) * | 1975-02-24 | 1977-11-01 | The Upjohn Company | 2,2-Difluoro-16-phenoxy-PGA2 analogs |
| US4056557A (en) * | 1975-02-24 | 1977-11-01 | The Upjohn Company | 2,2-Difluoro-16-phenoxy-PGF1 analogs |
| US4056556A (en) * | 1975-02-24 | 1977-11-01 | The Upjohn Company | 2,2-Difluoro-16-phenoxy-PGE2 analogs |
| US4056554A (en) * | 1975-02-24 | 1977-11-01 | The Upjohn Company | 2,2-Difluoro-16-phenoxy-13,14-dihydro-PGF1, analogs |
| US4059614A (en) * | 1975-02-24 | 1977-11-22 | The Upjohn Company | 2,2-Difluoro-16-phenoxy-PGE1 analogs |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4008263A (en) * | 1969-03-14 | 1977-02-15 | The Upjohn Company | Racemic fluoro-substituted PGF2 .sub.α analogs |
| US3993687A (en) * | 1969-03-14 | 1976-11-23 | The Upjohn Company | Racemic fluoro-substituted PGB2 analogs |
| US3983153A (en) * | 1969-03-14 | 1976-09-28 | The Upjohn Company | Racemic fluoro-substituted PGE2 analogs |
| US3940438A (en) * | 1971-05-24 | 1976-02-24 | Alza Corporation | Crystalline racemic 9α,11α,15(S)-trihydroxy-5-cis,13-trans-prostadienoic acid |
| US3988361A (en) * | 1971-11-16 | 1976-10-26 | The Upjohn Company | 8β-PGE2 and related compounds |
| GB1396206A (en) * | 1972-04-27 | 1975-06-04 | Upjohn Co | Prostaglandins and the preparation thereof |
| US4053502A (en) * | 1975-10-02 | 1977-10-11 | The Upjohn Company | 4,4,5,5-Tetradehydro-ω-aryl-PGE1 analogs |
| US4013695A (en) * | 1975-10-02 | 1977-03-22 | The Upjohn Company | 4,4,5,5-Tetradehydro-PGE1 analogs |
| US4053500A (en) * | 1975-10-02 | 1977-10-11 | The Upjohn Company | 4,4,5,5-Tetradehydro-ω-aryl-PGF1α analogs |
| US5990168A (en) * | 1996-04-18 | 1999-11-23 | Alberta Cancer Board | Methods and compositions for the treatment of ataxia telangiectasia |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3069322A (en) * | 1958-05-28 | 1962-12-18 | Bergstrom Sune | Pge and pgf |
-
1969
- 1969-12-12 BR BR215068/69A patent/BR6915068D0/en unknown
-
1970
- 1970-02-19 CA CA075,313A patent/CA968348A/en not_active Expired
- 1970-02-23 IL IL33949A patent/IL33949A/en unknown
- 1970-03-05 CH CH322870A patent/CH549549A/en not_active IP Right Cessation
- 1970-03-05 CH CH1773672A patent/CH553740A/en not_active IP Right Cessation
- 1970-03-05 CH CH1773772A patent/CH553739A/en not_active IP Right Cessation
- 1970-03-09 NL NL7003298A patent/NL7003298A/xx unknown
- 1970-03-10 ES ES377342A patent/ES377342A1/en not_active Expired
- 1970-03-10 GB GB01510/70A patent/GB1282661A/en not_active Expired
- 1970-03-10 GB GB58026/71A patent/GB1282662A/en not_active Expired
- 1970-03-13 FR FR7009184A patent/FR2034951B1/fr not_active Expired
- 1970-03-13 BE BE747348D patent/BE747348A/en not_active IP Right Cessation
- 1970-03-13 DE DE19702011969 patent/DE2011969A1/en active Pending
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4001300A (en) * | 1975-02-24 | 1977-01-04 | The Upjohn Company | 2,2-Difluoro-16-phenoxy-PGF2 analogs |
| US4056555A (en) * | 1975-02-24 | 1977-11-01 | The Upjohn Company | 2,2-Difluoro-16-phenoxy-PGA2 analogs |
| US4056557A (en) * | 1975-02-24 | 1977-11-01 | The Upjohn Company | 2,2-Difluoro-16-phenoxy-PGF1 analogs |
| US4056556A (en) * | 1975-02-24 | 1977-11-01 | The Upjohn Company | 2,2-Difluoro-16-phenoxy-PGE2 analogs |
| US4056554A (en) * | 1975-02-24 | 1977-11-01 | The Upjohn Company | 2,2-Difluoro-16-phenoxy-13,14-dihydro-PGF1, analogs |
| US4057574A (en) * | 1975-02-24 | 1977-11-08 | The Upjohn Company | 2,2-Difluoro-16-phenoxy-13,14-dihydro-PGA2 analogs |
| US4059614A (en) * | 1975-02-24 | 1977-11-22 | The Upjohn Company | 2,2-Difluoro-16-phenoxy-PGE1 analogs |
| US4064160A (en) * | 1975-02-24 | 1977-12-20 | The Upjohn Company | 2,2-Difluoro-16-phenoxy-13,14 dihydro-PGE, analogs |
| US4097519A (en) * | 1975-02-24 | 1978-06-27 | The Upjohn Company | 2,2-Difluoro-16-phenoxy-PGA1 analogs |
Also Published As
| Publication number | Publication date |
|---|---|
| CA968348A (en) | 1975-05-27 |
| CH553739A (en) | 1974-09-13 |
| GB1282662A (en) | 1972-07-19 |
| BE747348A (en) | 1970-09-14 |
| ES377342A1 (en) | 1973-01-01 |
| NL7003298A (en) | 1970-09-16 |
| FR2034951A1 (en) | 1970-12-18 |
| CH549549A (en) | 1974-05-31 |
| IL33949A0 (en) | 1970-05-21 |
| CH553740A (en) | 1974-09-13 |
| IL33949A (en) | 1976-06-30 |
| FR2034951B1 (en) | 1974-02-01 |
| DE2011969A1 (en) | 1970-10-08 |
| BR6915068D0 (en) | 1973-05-24 |
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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 |