DE2147316A1 - 15-Oxoprost-13-ensäurederivate und Verfahren zur Herstellung derselben - Google Patents
15-Oxoprost-13-ensäurederivate und Verfahren zur Herstellung derselbenInfo
- Publication number
- DE2147316A1 DE2147316A1 DE19712147316 DE2147316A DE2147316A1 DE 2147316 A1 DE2147316 A1 DE 2147316A1 DE 19712147316 DE19712147316 DE 19712147316 DE 2147316 A DE2147316 A DE 2147316A DE 2147316 A1 DE2147316 A1 DE 2147316A1
- Authority
- DE
- Germany
- Prior art keywords
- carbon atoms
- group
- straight
- reaction
- oxoprost
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 16
- WFZQQEYPOJMCSS-ZWKOTPCHSA-N 7-[(1S,2S)-2-(3-oxooct-1-enyl)cyclopentyl]heptanoic acid Chemical class O=C(C=C[C@H]1CCC[C@@H]1CCCCCCC(=O)O)CCCCC WFZQQEYPOJMCSS-ZWKOTPCHSA-N 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims 2
- 239000002904 solvent Substances 0.000 claims description 38
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 36
- 238000006243 chemical reaction Methods 0.000 claims description 24
- -1 phosphorane compound Chemical class 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 150000004702 methyl esters Chemical class 0.000 claims description 5
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 239000007795 chemical reaction product Substances 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 4
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 4
- RALDHUZFXJKFQB-UHFFFAOYSA-N cyclopentene-1-carbaldehyde Chemical class O=CC1=CCCC1 RALDHUZFXJKFQB-UHFFFAOYSA-N 0.000 claims description 3
- 125000004979 cyclopentylene group Chemical group 0.000 claims description 3
- 238000010992 reflux Methods 0.000 claims description 3
- 230000003301 hydrolyzing effect Effects 0.000 claims description 2
- VJNNWEGXWQHZJW-RBUKOAKNSA-N methyl 7-[(1S,2S)-2-(3-oxooct-1-enyl)cyclopentyl]heptanoate Chemical compound O=C(C=C[C@H]1CCC[C@@H]1CCCCCCC(=O)OC)CCCCC VJNNWEGXWQHZJW-RBUKOAKNSA-N 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- VELDYOPRLMJFIK-UHFFFAOYSA-N cyclopentanecarbaldehyde Chemical compound O=CC1CCCC1 VELDYOPRLMJFIK-UHFFFAOYSA-N 0.000 claims 1
- 125000001033 ether group Chemical group 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- QQHAYFDWXYVLFM-XRRBNZLQSA-N methyl 7-[(1S,2S)-3-hydroxy-2-(3-oxooct-1-enyl)cyclopentyl]heptanoate Chemical compound OC1CC[C@H](CCCCCCC(=O)OC)[C@H]1C=CC(CCCCC)=O QQHAYFDWXYVLFM-XRRBNZLQSA-N 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 63
- 239000000203 mixture Substances 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 238000001819 mass spectrum Methods 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 238000002211 ultraviolet spectrum Methods 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 238000002329 infrared spectrum Methods 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- 239000003929 acidic solution Substances 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
- 235000011054 acetic acid Nutrition 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- XWIXJUDKSVADDF-PAMZHZACSA-N 7-[(1s,2s)-2-(3-hydroxyoct-1-enyl)cyclopentyl]heptanoic acid Chemical class CCCCCC(O)C=C[C@H]1CCC[C@@H]1CCCCCCC(O)=O XWIXJUDKSVADDF-PAMZHZACSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
- 150000003180 prostaglandins Chemical class 0.000 description 3
- DERLEQYHZCMIPL-UHFFFAOYSA-N 1-(triphenyl-$l^{5}-phosphanylidene)heptan-2-one Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=CC(=O)CCCCC)C1=CC=CC=C1 DERLEQYHZCMIPL-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 208000036029 Uterine contractions during pregnancy Diseases 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 230000003405 preventing effect Effects 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000006722 reduction reaction Methods 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- MZZGLPCJQGFUIN-UHFFFAOYSA-N 1-(tributyl-$l^{5}-phosphanylidene)heptan-2-one Chemical compound CCCCCC(=O)C=P(CCCC)(CCCC)CCCC MZZGLPCJQGFUIN-UHFFFAOYSA-N 0.000 description 1
- 108010051913 15-hydroxyprostaglandin dehydrogenase Proteins 0.000 description 1
- 102100030489 15-hydroxyprostaglandin dehydrogenase [NAD(+)] Human genes 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- XLFGFYRDTOAYFX-UHFFFAOYSA-N 7-(2-formyl-3-hydroxycyclopentyl)heptanoic acid Chemical compound C(=O)C1C(CCC1O)CCCCCCC(=O)O XLFGFYRDTOAYFX-UHFFFAOYSA-N 0.000 description 1
- SPXILGOITDKINO-UHFFFAOYSA-N 7-(2-formylcyclopenten-1-yl)heptanoic acid Chemical compound OC(=O)CCCCCCC1=C(CCC1)C=O SPXILGOITDKINO-UHFFFAOYSA-N 0.000 description 1
- HEXXDVNJCRIFEJ-CXEJCQMISA-N CCCCCC(C=C[C@H]([C@@H](CCCCCCC(O)=O)CC1)C1O)=O Chemical compound CCCCCC(C=C[C@H]([C@@H](CCCCCCC(O)=O)CC1)C1O)=O HEXXDVNJCRIFEJ-CXEJCQMISA-N 0.000 description 1
- 101710088194 Dehydrogenase Proteins 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound 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 description 1
- 241000700159 Rattus Species 0.000 description 1
- 238000007239 Wittig reaction Methods 0.000 description 1
- 206010000210 abortion Diseases 0.000 description 1
- 231100000176 abortion Toxicity 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
- 229910001863 barium hydroxide Inorganic materials 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- XEYBRNLFEZDVAW-ARSRFYASSA-N dinoprostone Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O XEYBRNLFEZDVAW-ARSRFYASSA-N 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- YMLLRRIZEHHHPW-UHFFFAOYSA-N heptylidene(triphenyl)-$l^{5}-phosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=CCCCCCC)C1=CC=CC=C1 YMLLRRIZEHHHPW-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 238000004890 malting Methods 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- UDWFHJFHUPLROQ-UHFFFAOYSA-N methyl 7-(2-formylcyclopenten-1-yl)heptanoate Chemical compound COC(=O)CCCCCCC1=C(C=O)CCC1 UDWFHJFHUPLROQ-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229940094443 oxytocics prostaglandins Drugs 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- ZMRUPTIKESYGQW-UHFFFAOYSA-N propranolol hydrochloride Chemical compound [H+].[Cl-].C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 ZMRUPTIKESYGQW-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 210000004291 uterus Anatomy 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP45082238A JPS514990B1 (xx) | 1970-09-19 | 1970-09-19 | |
| JP8480070A JPS4928749B1 (xx) | 1970-09-28 | 1970-09-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2147316A1 true DE2147316A1 (de) | 1972-05-25 |
Family
ID=26423252
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712147316 Pending DE2147316A1 (de) | 1970-09-19 | 1971-09-18 | 15-Oxoprost-13-ensäurederivate und Verfahren zur Herstellung derselben |
| DE19712147315 Pending DE2147315A1 (de) | 1970-09-19 | 1971-09-18 | Prostaglandinderivate und Verfahren zur Herstellung derselben |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712147315 Pending DE2147315A1 (de) | 1970-09-19 | 1971-09-18 | Prostaglandinderivate und Verfahren zur Herstellung derselben |
Country Status (7)
| Country | Link |
|---|---|
| BE (2) | BE772837A (xx) |
| CA (2) | CA951723A (xx) |
| DE (2) | DE2147316A1 (xx) |
| FR (2) | FR2106630B1 (xx) |
| GB (2) | GB1351533A (xx) |
| NL (2) | NL7112746A (xx) |
| SE (2) | SE375089B (xx) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3887587A (en) * | 1972-04-17 | 1975-06-03 | Pfizer | Synthesis of prostaglandins of the one-series |
-
1971
- 1971-09-15 CA CA122,916,A patent/CA951723A/en not_active Expired
- 1971-09-16 CA CA123,024A patent/CA974987A/en not_active Expired
- 1971-09-16 NL NL7112746A patent/NL7112746A/xx unknown
- 1971-09-17 NL NL7112804A patent/NL7112804A/xx unknown
- 1971-09-17 SE SE1183671A patent/SE375089B/xx unknown
- 1971-09-17 SE SE1183771A patent/SE375090B/xx unknown
- 1971-09-18 DE DE19712147316 patent/DE2147316A1/de active Pending
- 1971-09-18 DE DE19712147315 patent/DE2147315A1/de active Pending
- 1971-09-20 GB GB4381071A patent/GB1351533A/en not_active Expired
- 1971-09-20 FR FR7133683A patent/FR2106630B1/fr not_active Expired
- 1971-09-20 FR FR7133684A patent/FR2106631B1/fr not_active Expired
- 1971-09-20 BE BE772837A patent/BE772837A/xx unknown
- 1971-09-20 GB GB4380771A patent/GB1351532A/en not_active Expired
- 1971-09-20 BE BE772836A patent/BE772836A/nl unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BE772837A (fr) | 1972-01-17 |
| NL7112804A (xx) | 1972-03-21 |
| GB1351532A (en) | 1974-05-01 |
| CA951723A (en) | 1974-07-23 |
| CA974987A (en) | 1975-09-23 |
| GB1351533A (en) | 1974-05-01 |
| DE2147315A1 (de) | 1972-03-23 |
| FR2106631A1 (xx) | 1972-05-05 |
| FR2106630B1 (xx) | 1975-08-01 |
| FR2106631B1 (xx) | 1975-08-01 |
| SE375089B (xx) | 1975-04-07 |
| NL7112746A (xx) | 1972-03-21 |
| BE772836A (nl) | 1972-01-17 |
| SE375090B (xx) | 1975-04-07 |
| FR2106630A1 (xx) | 1972-05-05 |
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