CH637948A5 - Process for the preparation of prostaglandin derivatives - Google Patents
Process for the preparation of prostaglandin derivatives Download PDFInfo
- Publication number
- CH637948A5 CH637948A5 CH583777A CH583777A CH637948A5 CH 637948 A5 CH637948 A5 CH 637948A5 CH 583777 A CH583777 A CH 583777A CH 583777 A CH583777 A CH 583777A CH 637948 A5 CH637948 A5 CH 637948A5
- Authority
- CH
- Switzerland
- Prior art keywords
- compound
- formula
- hydrogen
- sodium
- prostacyclin
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 26
- 238000002360 preparation method Methods 0.000 title claims description 6
- 150000003180 prostaglandins Chemical class 0.000 title description 20
- 150000001875 compounds Chemical class 0.000 claims description 29
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 26
- 239000001257 hydrogen Substances 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 13
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 12
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 239000011734 sodium Substances 0.000 claims description 7
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 6
- 150000001768 cations Chemical class 0.000 claims description 6
- 125000006239 protecting group Chemical group 0.000 claims description 6
- 229910052708 sodium Inorganic materials 0.000 claims description 6
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 5
- -1 alkali metal alkoxide Chemical class 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 150000002431 hydrogen Chemical group 0.000 claims description 5
- 229910052740 iodine Inorganic materials 0.000 claims description 5
- 239000011630 iodine Substances 0.000 claims description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 238000006704 dehydrohalogenation reaction Methods 0.000 claims description 4
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- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims description 3
- DKNPRRRKHAEUMW-UHFFFAOYSA-N Iodine aqueous Chemical compound [K+].I[I-]I DKNPRRRKHAEUMW-UHFFFAOYSA-N 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
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- 229940020414 potassium triiodide Drugs 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
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- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
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- 150000004702 methyl esters Chemical class 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
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- YIBNHAJFJUQSRA-YNNPMVKQSA-N prostaglandin H2 Chemical compound C1[C@@H]2OO[C@H]1[C@H](/C=C/[C@@H](O)CCCCC)[C@H]2C\C=C/CCCC(O)=O YIBNHAJFJUQSRA-YNNPMVKQSA-N 0.000 description 6
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- 101000988802 Homo sapiens Hematopoietic prostaglandin D synthase Proteins 0.000 description 5
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- BHMBVRSPMRCCGG-OUTUXVNYSA-N prostaglandin D2 Chemical compound CCCCC[C@H](O)\C=C\[C@@H]1[C@@H](C\C=C/CCCC(O)=O)[C@@H](O)CC1=O BHMBVRSPMRCCGG-OUTUXVNYSA-N 0.000 description 5
- BHMBVRSPMRCCGG-UHFFFAOYSA-N prostaglandine D2 Natural products CCCCCC(O)C=CC1C(CC=CCCCC(O)=O)C(O)CC1=O BHMBVRSPMRCCGG-UHFFFAOYSA-N 0.000 description 5
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- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
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Classifications
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- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- 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
- C07D307/937—Not further condensed cyclopenta [b] furans or hydrogenated cyclopenta [b] furans with hydrocarbon or substituted hydrocarbon radicals directly attached in position 2, e.g. prostacyclins
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Furan Compounds (AREA)
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB19384/76A GB1583961A (en) | 1976-05-11 | 1976-05-11 | Prostacyclin and derivatives thereof |
| GB3415176 | 1976-08-17 | ||
| GB3654776 | 1976-09-03 | ||
| GB4344576 | 1976-10-20 | ||
| GB5306076 | 1976-12-20 | ||
| GB1338977 | 1977-03-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH637948A5 true CH637948A5 (en) | 1983-08-31 |
Family
ID=27546654
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH583777A CH637948A5 (en) | 1976-05-11 | 1977-05-10 | Process for the preparation of prostaglandin derivatives |
Country Status (12)
| Country | Link |
|---|---|
| JP (1) | JPS52136161A (enExample) |
| BE (1) | BE854463A (enExample) |
| CH (1) | CH637948A5 (enExample) |
| DE (1) | DE2720999C2 (enExample) |
| DK (1) | DK149953C (enExample) |
| FR (1) | FR2351111A1 (enExample) |
| GB (1) | GB1583961A (enExample) |
| IE (1) | IE46036B1 (enExample) |
| IL (1) | IL52053A (enExample) |
| NL (1) | NL181973C (enExample) |
| NZ (1) | NZ184057A (enExample) |
| SE (1) | SE436647B (enExample) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI71138C (fi) * | 1976-12-31 | 1986-11-24 | Erba Farmitalia | Foerfarande foer framstaellning av terapeutiskt aktiva bisykliska prostaglandiner |
| US4178367A (en) | 1977-02-21 | 1979-12-11 | Ono Pharmaceutical Co. Ltd. | Prostaglandin I2 analogues |
| HU182583B (en) * | 1977-03-01 | 1984-02-28 | Chinoin Gyogyszer Es Vegyeszet | Process for preparing prostacyclin and analogues thereof |
| DE2743283A1 (de) * | 1977-09-27 | 1979-04-05 | Hoechst Ag | Neue prostacyclin-analoga |
| IT1088036B (it) | 1977-11-25 | 1985-06-04 | Erba Carlo Spa | 15-epi-prostaciclina e prostaciclina analoghi |
| DE2811950A1 (de) * | 1978-03-18 | 1979-12-13 | Hoechst Ag | Neue analoga von prostacyclin |
| ZA787353B (en) * | 1978-05-17 | 1980-08-27 | Wellcome Found | Pharmaceutical formulations |
| US4430340A (en) * | 1978-07-17 | 1984-02-07 | The Upjohn Company | Stabilization of PGI2 compounds with surfactants |
| IL58384A0 (en) | 1978-10-14 | 1980-01-31 | Beecham Group Ltd | 12-aza analogues of prostcyclin their preparation and pharmaceutical composition containing them |
| ZA815504B (en) * | 1980-09-15 | 1982-08-25 | Upjohn Co | Crystalline pgi2 methyl ester |
| CH651033A5 (de) * | 1981-03-11 | 1985-08-30 | Hoffmann La Roche | Fluorprostacycline. |
| DE3438870A1 (de) * | 1983-12-13 | 1985-06-13 | Stellmacher, Gerhard, Ing.(grad.), 8501 Schwaig | Spannvorrichtung fuer holzbearbeitungsmaschinen |
| JP5697260B2 (ja) | 2009-11-13 | 2015-04-08 | 東レ株式会社 | 糖尿病の治療または予防薬 |
| HU231031B1 (hu) | 2016-03-23 | 2019-12-30 | CHINOIN Gyógyszer és Vegyészeti Termékek Gyára Zrt. | Megnövelt stabilitású epoprostenol nátrium és eljárás előállítására |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL51189A (en) * | 1976-02-04 | 1985-08-30 | Upjohn Co | Prostaglandin analogs |
-
1976
- 1976-05-11 GB GB19384/76A patent/GB1583961A/en not_active Expired
-
1977
- 1977-04-07 FR FR7710593A patent/FR2351111A1/fr not_active Withdrawn
- 1977-05-10 IE IE950/77A patent/IE46036B1/en not_active IP Right Cessation
- 1977-05-10 BE BE177444A patent/BE854463A/xx not_active IP Right Cessation
- 1977-05-10 DK DK205377A patent/DK149953C/da not_active IP Right Cessation
- 1977-05-10 SE SE7705423A patent/SE436647B/xx not_active IP Right Cessation
- 1977-05-10 IL IL52053A patent/IL52053A/xx unknown
- 1977-05-10 NZ NZ184057A patent/NZ184057A/xx unknown
- 1977-05-10 DE DE2720999A patent/DE2720999C2/de not_active Expired
- 1977-05-10 NL NLAANVRAGE7705141,A patent/NL181973C/xx not_active IP Right Cessation
- 1977-05-10 JP JP5361977A patent/JPS52136161A/ja active Granted
- 1977-05-10 CH CH583777A patent/CH637948A5/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| IE46036L (en) | 1977-11-11 |
| JPS52136161A (en) | 1977-11-14 |
| GB1583961A (en) | 1981-02-04 |
| IE46036B1 (en) | 1983-02-09 |
| NL181973B (nl) | 1987-07-16 |
| SE7705423L (sv) | 1977-11-12 |
| IL52053A (en) | 1983-09-30 |
| DE2720999A1 (de) | 1977-11-24 |
| SE436647B (sv) | 1985-01-14 |
| NZ184057A (en) | 1979-10-25 |
| DK149953C (da) | 1987-06-29 |
| JPS619953B2 (enExample) | 1986-03-27 |
| NL181973C (nl) | 1987-12-16 |
| IL52053A0 (en) | 1977-07-31 |
| FR2351111A1 (fr) | 1977-12-09 |
| NL7705141A (nl) | 1977-11-15 |
| BE854463A (fr) | 1977-11-10 |
| DE2720999C2 (de) | 1986-09-18 |
| DK149953B (da) | 1986-11-03 |
| DK205377A (da) | 1977-11-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |