DE2328131C3 - Neues Verfahren zur Herstellung von Prostaglandin-F↓2↓↓α↓ und seinen Analogen - Google Patents
Neues Verfahren zur Herstellung von Prostaglandin-F↓2↓↓α↓ und seinen AnalogenInfo
- Publication number
- DE2328131C3 DE2328131C3 DE2328131A DE2328131A DE2328131C3 DE 2328131 C3 DE2328131 C3 DE 2328131C3 DE 2328131 A DE2328131 A DE 2328131A DE 2328131 A DE2328131 A DE 2328131A DE 2328131 C3 DE2328131 C3 DE 2328131C3
- Authority
- DE
- Germany
- Prior art keywords
- prostaglandin
- analogues
- formula
- production
- new process
- 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
- 238000000034 method Methods 0.000 title claims description 7
- DZUXGQBLFALXCR-UHFFFAOYSA-N (+)-(9alpha,11alpha,13E,15S)-9,11,15-trihydroxyprost-13-en-1-oic acid Natural products CCCCCC(O)C=CC1C(O)CC(O)C1CCCCCCC(O)=O DZUXGQBLFALXCR-UHFFFAOYSA-N 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 150000003180 prostaglandins Chemical class 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 150000002596 lactones Chemical class 0.000 claims description 6
- PXGPLTODNUVGFL-BRIYLRKRSA-N (E,Z)-(1R,2R,3R,5S)-7-(3,5-Dihydroxy-2-((3S)-(3-hydroxy-1-octenyl))cyclopentyl)-5-heptenoic acid Chemical compound CCCCC[C@H](O)C=C[C@H]1[C@H](O)C[C@H](O)[C@@H]1CC=CCCCC(O)=O PXGPLTODNUVGFL-BRIYLRKRSA-N 0.000 claims description 5
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- -1 lithium tri-tert-butoxyaluminum hydride Chemical class 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000003153 chemical reaction reagent Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- AXCHZLOJGKSWLV-UHFFFAOYSA-N (4-phenylphenyl)methanol Chemical compound C1=CC(CO)=CC=C1C1=CC=CC=C1 AXCHZLOJGKSWLV-UHFFFAOYSA-N 0.000 description 2
- MLOSJPZSZWUDSK-UHFFFAOYSA-N 4-carboxybutyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCCCC(=O)O)C1=CC=CC=C1 MLOSJPZSZWUDSK-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 239000000010 aprotic solvent Substances 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- HUHXLHLWASNVDB-UHFFFAOYSA-N 2-(oxan-2-yloxy)oxane Chemical compound O1CCCCC1OC1OCCCC1 HUHXLHLWASNVDB-UHFFFAOYSA-N 0.000 description 1
- JLGWNXOPHLMKAY-UHFFFAOYSA-N C(C)(C)(C)[Li].[K] Chemical compound C(C)(C)(C)[Li].[K] JLGWNXOPHLMKAY-UHFFFAOYSA-N 0.000 description 1
- BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- 241001024304 Mino Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 229960001342 dinoprost Drugs 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003104 hexanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 125000000686 lactone group Chemical group 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000003232 p-nitrobenzoyl group Chemical group [N+](=O)([O-])C1=CC=C(C(=O)*)C=C1 0.000 description 1
- 125000005440 p-toluyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C(*)=O)C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- CWXOAQXKPAENDI-UHFFFAOYSA-N sodium methylsulfinylmethylide Chemical compound [Na+].CS([CH2-])=O CWXOAQXKPAENDI-UHFFFAOYSA-N 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (13)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2328131A DE2328131C3 (de) | 1973-05-30 | 1973-05-30 | Neues Verfahren zur Herstellung von Prostaglandin-F↓2↓↓α↓ und seinen Analogen |
| US05/472,737 US3970692A (en) | 1973-05-30 | 1974-05-23 | Process for the preparation of prostaglandin F2.sub.α and the analogs thereof |
| GB2309374A GB1473670A (en) | 1973-05-30 | 1974-05-23 | Process for the manufacture of prostaglandin-f2a and analogues thereof |
| DK286074A DK286074A (en, 2012) | 1973-05-30 | 1974-05-27 | |
| CA200,881A CA1030534A (en) | 1973-05-30 | 1974-05-27 | Process for producing prostaglandin-f2a and analogues thereof |
| JP49059585A JPS5747911B2 (en, 2012) | 1973-05-30 | 1974-05-27 | |
| DD178808A DD111895A5 (en, 2012) | 1973-05-30 | 1974-05-28 | |
| SE7407100A SE7407100L (en, 2012) | 1973-05-30 | 1974-05-29 | |
| FR7418613A FR2231655B1 (en, 2012) | 1973-05-30 | 1974-05-29 | |
| HU74SC475A HU173114B (hu) | 1973-05-30 | 1974-05-29 | Novyj sposob poluchenija f vniz 2 al'fa prostaglandina i ego analogov |
| NL7407271A NL7407271A (en, 2012) | 1973-05-30 | 1974-05-30 | |
| CH740974A CH599148A5 (en, 2012) | 1973-05-30 | 1974-05-30 | |
| BE144919A BE815741A (fr) | 1973-05-30 | 1974-05-30 | Procede de preparation de prostaglandine-f2alpha et de ses analogues |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2328131A DE2328131C3 (de) | 1973-05-30 | 1973-05-30 | Neues Verfahren zur Herstellung von Prostaglandin-F↓2↓↓α↓ und seinen Analogen |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2328131A1 DE2328131A1 (de) | 1975-01-02 |
| DE2328131B2 DE2328131B2 (de) | 1980-10-02 |
| DE2328131C3 true DE2328131C3 (de) | 1986-11-13 |
Family
ID=5882871
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2328131A Expired DE2328131C3 (de) | 1973-05-30 | 1973-05-30 | Neues Verfahren zur Herstellung von Prostaglandin-F↓2↓↓α↓ und seinen Analogen |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US3970692A (en, 2012) |
| JP (1) | JPS5747911B2 (en, 2012) |
| BE (1) | BE815741A (en, 2012) |
| CA (1) | CA1030534A (en, 2012) |
| CH (1) | CH599148A5 (en, 2012) |
| DD (1) | DD111895A5 (en, 2012) |
| DE (1) | DE2328131C3 (en, 2012) |
| DK (1) | DK286074A (en, 2012) |
| FR (1) | FR2231655B1 (en, 2012) |
| GB (1) | GB1473670A (en, 2012) |
| HU (1) | HU173114B (en, 2012) |
| NL (1) | NL7407271A (en, 2012) |
| SE (1) | SE7407100L (en, 2012) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2508826A1 (de) | 1975-02-27 | 1976-09-09 | Schering Ag | Neue 1,3-benzodioxan-prostansaeurederivate und verfahren zu ihrer herstellung |
| JPS62145512U (en, 2012) * | 1986-03-11 | 1987-09-14 | ||
| HU231203B1 (hu) * | 2011-12-21 | 2021-10-28 | CHINOIN Gyógyszer és Vegyészeti Termékek Gyára Zrt. | Új eljárás travoprost előállítására |
| KR101150310B1 (ko) * | 2012-01-26 | 2012-05-29 | (주) 현진테크 | 야간 및 우천시 가시성능이 향상된 도로용 차선 및 이의 도색방법 |
| CN103750790B (zh) * | 2013-12-22 | 2016-06-29 | 浙江大学 | 一种扫动式发电储能照明扫帚 |
-
1973
- 1973-05-30 DE DE2328131A patent/DE2328131C3/de not_active Expired
-
1974
- 1974-05-23 GB GB2309374A patent/GB1473670A/en not_active Expired
- 1974-05-23 US US05/472,737 patent/US3970692A/en not_active Expired - Lifetime
- 1974-05-27 JP JP49059585A patent/JPS5747911B2/ja not_active Expired
- 1974-05-27 DK DK286074A patent/DK286074A/da not_active Application Discontinuation
- 1974-05-27 CA CA200,881A patent/CA1030534A/en not_active Expired
- 1974-05-28 DD DD178808A patent/DD111895A5/xx unknown
- 1974-05-29 HU HU74SC475A patent/HU173114B/hu unknown
- 1974-05-29 SE SE7407100A patent/SE7407100L/ not_active Application Discontinuation
- 1974-05-29 FR FR7418613A patent/FR2231655B1/fr not_active Expired
- 1974-05-30 CH CH740974A patent/CH599148A5/xx not_active IP Right Cessation
- 1974-05-30 NL NL7407271A patent/NL7407271A/xx not_active Application Discontinuation
- 1974-05-30 BE BE144919A patent/BE815741A/xx not_active IP Right Cessation
Non-Patent Citations (1)
| Title |
|---|
| NICHTS-ERMITTELT |
Also Published As
| Publication number | Publication date |
|---|---|
| US3970692A (en) | 1976-07-20 |
| DK286074A (en, 2012) | 1975-01-13 |
| HU173114B (hu) | 1979-02-28 |
| SE7407100L (en, 2012) | 1974-12-02 |
| DD111895A5 (en, 2012) | 1975-03-12 |
| DE2328131B2 (de) | 1980-10-02 |
| GB1473670A (en) | 1977-05-18 |
| FR2231655A1 (en, 2012) | 1974-12-27 |
| JPS5747911B2 (en, 2012) | 1982-10-13 |
| NL7407271A (en, 2012) | 1974-12-03 |
| FR2231655B1 (en, 2012) | 1977-09-30 |
| CH599148A5 (en, 2012) | 1978-05-12 |
| DE2328131A1 (de) | 1975-01-02 |
| JPS5019739A (en, 2012) | 1975-03-01 |
| BE815741A (fr) | 1974-12-02 |
| CA1030534A (en) | 1978-05-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| 8263 | Opposition against grant of a patent | ||
| 8281 | Inventor (new situation) |
Free format text: RADUECHEL, BERND, DR. SKUBALLA, WERNER, DR. VORBRUEGGEN, HELMUT, DR., 1000 BERLIN, DE |
|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |