DE2365999A1 - Cyclopentane zur herstellung von 15-substituierten-omega-pentanorprostaglandinen - Google Patents
Cyclopentane zur herstellung von 15-substituierten-omega-pentanorprostaglandinenInfo
- Publication number
- DE2365999A1 DE2365999A1 DE2365999A DE2365999A DE2365999A1 DE 2365999 A1 DE2365999 A1 DE 2365999A1 DE 2365999 A DE2365999 A DE 2365999A DE 2365999 A DE2365999 A DE 2365999A DE 2365999 A1 DE2365999 A1 DE 2365999A1
- Authority
- DE
- Germany
- Prior art keywords
- radical
- phenyl
- lower alkyl
- biphenyl
- cyclopentanes
- 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.)
- Withdrawn
Links
- 150000001940 cyclopentanes Chemical class 0.000 title description 2
- 238000004519 manufacturing process Methods 0.000 title description 2
- -1 alkyl radical Chemical class 0.000 claims description 21
- SXXLKZCNJHJYFL-UHFFFAOYSA-N 4,5,6,7-tetrahydro-[1,2]oxazolo[4,5-c]pyridin-5-ium-3-olate Chemical compound C1CNCC2=C1ONC2=O SXXLKZCNJHJYFL-UHFFFAOYSA-N 0.000 claims description 6
- 101000799461 Homo sapiens Thrombopoietin Proteins 0.000 claims description 6
- 102100034195 Thrombopoietin Human genes 0.000 claims description 6
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 5
- 150000003254 radicals Chemical class 0.000 claims description 3
- WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 150000003180 prostaglandins Chemical class 0.000 description 7
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 3
- YXVFYQXJAXKLAK-UHFFFAOYSA-N biphenyl-4-ol Chemical compound C1=CC(O)=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-N 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 230000032050 esterification Effects 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- WPHGSKGZRAQSGP-UHFFFAOYSA-N methylenecyclohexane Natural products C1CCCC2CC21 WPHGSKGZRAQSGP-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229940094443 oxytocics prostaglandins Drugs 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/24—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
-
- 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
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/54—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
- 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
- C07D317/44—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 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—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 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
- C07D317/54—Radicals substituted by oxygen atoms
-
- 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 System
- 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)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pyrane Compounds (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Furan Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US30481572A | 1972-11-08 | 1972-11-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2365999A1 true DE2365999A1 (de) | 1977-05-12 |
Family
ID=23178143
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2365999A Withdrawn DE2365999A1 (de) | 1972-11-08 | 1973-11-03 | Cyclopentane zur herstellung von 15-substituierten-omega-pentanorprostaglandinen |
| DE19732355042 Withdrawn DE2355042A1 (de) | 1972-11-08 | 1973-11-03 | Neue prostaglandinanaloge und verfahren zu deren herstellung |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19732355042 Withdrawn DE2355042A1 (de) | 1972-11-08 | 1973-11-03 | Neue prostaglandinanaloge und verfahren zu deren herstellung |
Country Status (24)
| Country | Link |
|---|---|
| JP (1) | JPS5644068B2 (hu) |
| AR (2) | AR204816A1 (hu) |
| AT (1) | AT347607B (hu) |
| BE (1) | BE807047A (hu) |
| CA (1) | CA1027559A (hu) |
| CH (1) | CH601222A5 (hu) |
| CS (1) | CS188175B2 (hu) |
| DD (2) | DD111370A5 (hu) |
| DE (2) | DE2365999A1 (hu) |
| ES (2) | ES420326A1 (hu) |
| FI (1) | FI58116C (hu) |
| FR (2) | FR2205339B1 (hu) |
| GB (1) | GB1456511A (hu) |
| HU (2) | HU171818B (hu) |
| IE (1) | IE39686B1 (hu) |
| IL (1) | IL43553A (hu) |
| IN (1) | IN139905B (hu) |
| NL (1) | NL7315240A (hu) |
| NO (2) | NO145437C (hu) |
| PH (2) | PH15504A (hu) |
| SE (2) | SE420198B (hu) |
| SU (2) | SU538659A3 (hu) |
| YU (2) | YU287973A (hu) |
| ZA (1) | ZA738593B (hu) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2361381A1 (fr) * | 1972-07-13 | 1978-03-10 | Pfizer | Ethers tetrahydropyranyliques, utiles comme intermediaires de synthese de prostaglandines |
| US3929862A (en) * | 1974-01-08 | 1975-12-30 | Upjohn Co | Substituted tolylesters of PGF{HD 2{B {60 |
| US3998869A (en) * | 1974-11-14 | 1976-12-21 | The Upjohn Company | Substituted anilide esters of 16-substituted PGE2 |
| DE2737807A1 (de) * | 1976-08-27 | 1978-03-09 | Pfizer | C tief 1 -p-biphenylester von omega-pentanorprostaglandinen |
| US6531504B2 (en) * | 2001-05-17 | 2003-03-11 | Allergan, Inc. | Prostanoic acid derivatives as agents for lowering intraocular pressure |
-
1973
- 1973-01-01 AR AR250900A patent/AR204816A1/es active
- 1973-11-01 SE SE7314885A patent/SE420198B/xx unknown
- 1973-11-01 GB GB5088973A patent/GB1456511A/en not_active Expired
- 1973-11-02 IL IL43553A patent/IL43553A/xx unknown
- 1973-11-03 DE DE2365999A patent/DE2365999A1/de not_active Withdrawn
- 1973-11-03 DE DE19732355042 patent/DE2355042A1/de not_active Withdrawn
- 1973-11-06 IN IN2443/CAL/73A patent/IN139905B/en unknown
- 1973-11-07 YU YU02879/73A patent/YU287973A/xx unknown
- 1973-11-07 CA CA185,201A patent/CA1027559A/en not_active Expired
- 1973-11-07 FI FI3444/73A patent/FI58116C/fi active
- 1973-11-07 NO NO4290/73A patent/NO145437C/no unknown
- 1973-11-07 NL NL7315240A patent/NL7315240A/xx not_active Application Discontinuation
- 1973-11-07 AT AT937173A patent/AT347607B/de not_active IP Right Cessation
- 1973-11-07 ES ES420326A patent/ES420326A1/es not_active Expired
- 1973-11-08 CS CS737670A patent/CS188175B2/cs unknown
- 1973-11-08 HU HU73PI00000400A patent/HU171818B/hu unknown
- 1973-11-08 PH PH15198A patent/PH15504A/en unknown
- 1973-11-08 JP JP12501173A patent/JPS5644068B2/ja not_active Expired
- 1973-11-08 HU HU73PI00000453A patent/HU171945B/hu unknown
- 1973-11-08 IE IE2013/73A patent/IE39686B1/xx unknown
- 1973-11-08 ZA ZA738593A patent/ZA738593B/xx unknown
- 1973-11-08 DD DD174537A patent/DD111370A5/xx unknown
- 1973-11-08 CH CH1570273A patent/CH601222A5/xx not_active IP Right Cessation
- 1973-11-08 DD DD180196*A patent/DD113211A5/xx unknown
- 1973-11-08 FR FR7339759A patent/FR2205339B1/fr not_active Expired
- 1973-11-08 BE BE1005489A patent/BE807047A/xx unknown
- 1973-11-11 SU SU1971421A patent/SU538659A3/ru active
-
1974
- 1974-07-31 AR AR254983A patent/AR202311A1/es active
- 1974-10-03 NO NO743588A patent/NO146280C/no unknown
-
1975
- 1975-02-13 ES ES434687A patent/ES434687A1/es not_active Expired
- 1975-03-20 SU SU752115232A patent/SU1021340A3/ru active
- 1975-08-18 FR FR7525565A patent/FR2275452A1/fr active Granted
-
1976
- 1976-03-12 PH PH18199A patent/PH13794A/en unknown
-
1977
- 1977-04-15 SE SE7704369A patent/SE7704369L/xx not_active Application Discontinuation
-
1980
- 1980-10-15 YU YU02644/80A patent/YU264480A/xx unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH632481A5 (de) | Verfahren zur herstellung eines optisch aktiven norpinens. | |
| DE1793767A1 (de) | Acetale und ein verfahren zu ihrer herstellung | |
| DE2365999A1 (de) | Cyclopentane zur herstellung von 15-substituierten-omega-pentanorprostaglandinen | |
| DE2104976C2 (de) | Ätherpolycarbonsäuren, ihre Herstellung und Verwendung | |
| DE2732107C2 (de) | Verfahren zur Herstellung von cyclischen Ketoessigsäureestern | |
| JPS609754B2 (ja) | ビシクロオクタン誘導体の製造法 | |
| DE2539116C2 (de) | ω-Nor-cycloalkyl-13,14-dehydro-prostaglandine, Verfahren zu ihrer Herstellung sowie sie enthaltende pharmazeutische Mittel | |
| DE2429766C2 (de) | Optisch aktive cyclische ortho-Ester und deren racemische Gemische, Verfahren zu deren Herstellung und deren Verwendung zur Herstellung von optisch aktiven bicyclischen Lactondiolen und deren racemischen Gemischen | |
| DE862892C (de) | Verfahren zur Herstellung von ª, ª-ungesaettigten Cyclopolymethylenketonen | |
| CH643838A5 (de) | 15-epi-prostacyclinderivate, verfahren zu ihrer herstellung und pharmazeutische praeparate. | |
| EP0305389B1 (de) | Verfahren zur synthese homochiraler fünf- und sechsring- zwischenprodukte | |
| DE1618310C3 (hu) | ||
| DE2429750C2 (de) | Optisch aktive tricyclische Diester und deren racemisches Gemisch, Verfahren zu deren Herstellung und deren Verwendung zur Herstellung von optisch aktiven tricyclischen 2S-Lactonglykolen und deren racemischem Gemisch | |
| CH628634A5 (de) | Verfahren zur herstellung von 2,2'-bis(3,4-epoxy-5-oxotetrahydropyran)aether und produkt. | |
| DE2626287A1 (de) | Prostanderivate, verfahren zu ihrer herstellung und sie enthaltende arzneimittelzusammensetzung | |
| DE3335389A1 (de) | 15-cycloaliphatische derivate von 13,14-didehydrocarboprostacyclinen, verfahren zu deren herstellung sowie pharmazeutische oder veterinaere mittel, die diese enthalten | |
| DE2262792C3 (de) | Verfahren zur Herstellung von 3,6-Dihydro-o-dioxinderivaten | |
| DE2166797C2 (de) | Optisch aktive tricyclische Lactonaldehyde und Verfahren zu deren Herstellung | |
| AT359659B (de) | Verfahren zur herstellung eines neuen cyclopentanderivats | |
| AT367759B (de) | Verfahren zur herstellung neuer 1,3-oxathiolanyl- bzw. 1,3-oxathianylcyclopentanderivate | |
| DE2065277C3 (de) | Verfahren zur Herstellung von beta-Halogenäthansulfinaten. Ausscheidung aus: 2005514 | |
| DE2660902C2 (de) | Dicarbonsäure-bis[3,5-bis(chlorcarbonyl)-2,4,6-trijodanilid]- Verbindungen und deren Herstellung | |
| DE2321122C3 (de) | Verfahren zur Herstellung von Carbonsäurechloriden | |
| DE2640692B2 (hu) | ||
| AT205020B (de) | Verfahren zur Herstellung von neuen Verbindungen der Bicycloheptanreihe |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| 8176 | Proceedings suspended because of application no: |
Ref document number: 2355042 Country of ref document: DE Format of ref document f/p: P |
|
| 8178 | Suspension cancelled | ||
| 8130 | Withdrawal |