DE2129507C3 - Verfahren zur Herstellung von 8-Alkoxy-3halogenmethyl-4-acetoxy- 10-methylen-2,9dioxatricyclo(43,l,03 7 )decanen - Google Patents
Verfahren zur Herstellung von 8-Alkoxy-3halogenmethyl-4-acetoxy- 10-methylen-2,9dioxatricyclo(43,l,03 7 )decanenInfo
- Publication number
- DE2129507C3 DE2129507C3 DE19712129507 DE2129507A DE2129507C3 DE 2129507 C3 DE2129507 C3 DE 2129507C3 DE 19712129507 DE19712129507 DE 19712129507 DE 2129507 A DE2129507 A DE 2129507A DE 2129507 C3 DE2129507 C3 DE 2129507C3
- Authority
- DE
- Germany
- Prior art keywords
- ococh
- acetoxy
- methylene
- formula
- alkoxy
- 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 4
- 238000002360 preparation method Methods 0.000 title claims 5
- PHHROXLDZHUIGO-UHFFFAOYSA-N dihydrovaltrate Natural products CC(C)CC(=O)OCC1=COC(OC(=O)CC(C)C)C2C1CC(OC(C)=O)C21CO1 PHHROXLDZHUIGO-UHFFFAOYSA-N 0.000 claims description 16
- PHHROXLDZHUIGO-PNBTUHDLSA-N Didrovaltratum Chemical compound C([C@@]12[C@@H](OC(C)=O)C[C@H]3[C@@H]1[C@H](OC(=O)CC(C)C)OC=C3COC(=O)CC(C)C)O2 PHHROXLDZHUIGO-PNBTUHDLSA-N 0.000 claims description 15
- KQEOKUJOWVGWDX-UHFFFAOYSA-N Isodihydrovaltrate Natural products CC(C)CC(=O)OC1CC(C(=COC2OC(=O)CC(C)C)COC(C)=O)C2C11CO1 KQEOKUJOWVGWDX-UHFFFAOYSA-N 0.000 claims description 7
- 229950005934 didrovaltrate Drugs 0.000 claims description 7
- PVKOJQHHDYMUEI-UHFFFAOYSA-N didrovaltrate Natural products CC(C)CC(=O)COC1=COC(OC(=O)CC(C)C)C2C1CC(OC(=O)C)C23CO3 PVKOJQHHDYMUEI-UHFFFAOYSA-N 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- LANCLZFYVLANQS-RHMPUOGUSA-N Valerosidatum Chemical compound O([C@H]([C@@H]1[C@](C)(O)[C@@H](O)C[C@@H]11)OC(=O)CC(C)C)C=C1CO[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O LANCLZFYVLANQS-RHMPUOGUSA-N 0.000 claims description 2
- JRRUATLDNQIXRC-UHFFFAOYSA-N valerosidatum Natural products CC(C)CC(=O)OC1OCC(COC2OC(CO)C(O)C(O)C2O)C3CC(O)C(C)(O)C13 JRRUATLDNQIXRC-UHFFFAOYSA-N 0.000 claims description 2
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims 2
- 101150065749 Churc1 gene Proteins 0.000 claims 2
- 102100038239 Protein Churchill Human genes 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 239000000284 extract Substances 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 239000004615 ingredient Substances 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000010696 ester oil Substances 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 239000003610 charcoal Substances 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- BDIAUFOIMFAIPU-KVJIRVJXSA-N Valtratum Chemical compound C([C@]12[C@@H]3C(C(=CO[C@H]3OC(=O)CC(C)C)COC(C)=O)=C[C@@H]1OC(=O)CC(C)C)O2 BDIAUFOIMFAIPU-KVJIRVJXSA-N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- -1 didrovaltrate halogen Chemical class 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 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
- BDIAUFOIMFAIPU-UHFFFAOYSA-N valepotriate Natural products CC(C)CC(=O)OC1C=C(C(=COC2OC(=O)CC(C)C)COC(C)=O)C2C11CO1 BDIAUFOIMFAIPU-UHFFFAOYSA-N 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- FWKBQAVMKVZEOT-STCFVSJZSA-N Acevaltrate Chemical compound C([C@]12[C@@H](OC(=O)CC(C)(C)OC(C)=O)C=C3C(COC(C)=O)=CO[C@H]([C@H]23)OC(=O)CC(C)C)O1 FWKBQAVMKVZEOT-STCFVSJZSA-N 0.000 description 1
- WQKBMPNNRRZQLG-UHFFFAOYSA-N Acevaltratum Natural products CC(C)CC(=O)OC1C=C(C(=COC2OC(=O)CC(C)(C)OC(C)=O)COC(C)=O)C2C11CO1 WQKBMPNNRRZQLG-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 1
- 241000792914 Valeriana Species 0.000 description 1
- 241000606265 Valeriana jatamansi Species 0.000 description 1
- 244000126014 Valeriana officinalis Species 0.000 description 1
- 235000013832 Valeriana officinalis Nutrition 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000000287 crude extract Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000002897 diene group Chemical group 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- VGTPCRGMBIAPIM-UHFFFAOYSA-M sodium thiocyanate Chemical compound [Na+].[S-]C#N VGTPCRGMBIAPIM-UHFFFAOYSA-M 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 229940068146 valepotriate Drugs 0.000 description 1
- 235000016788 valerian Nutrition 0.000 description 1
- 235000020767 valerian extract Nutrition 0.000 description 1
- 235000017468 valeriana Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/08—Bridged systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712129507 DE2129507C3 (de) | 1971-06-15 | 1971-06-15 | Verfahren zur Herstellung von 8-Alkoxy-3halogenmethyl-4-acetoxy- 10-methylen-2,9dioxatricyclo(43,l,03 7 )decanen |
| CH630072A CH572918A5 (OSRAM) | 1971-06-15 | 1972-04-27 | |
| ES402726A ES402726A1 (es) | 1971-06-15 | 1972-05-13 | Procedimiento para la preparacion de 2,9-dioxatriciclo-(4, 3, 1, 03,7) decanos. |
| DD16329372A DD99784A1 (OSRAM) | 1971-06-15 | 1972-05-30 | |
| CS394072A CS167350B2 (OSRAM) | 1971-06-15 | 1972-06-07 | |
| JP5729172A JPS5538355B1 (OSRAM) | 1971-06-15 | 1972-06-08 | |
| AT511772A AT315869B (de) | 1971-06-15 | 1972-06-14 | Verfahren zur Herstellung von 2,9-Dioxatricyclo-(4,3,1,0<3,7>)decanen |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712129507 DE2129507C3 (de) | 1971-06-15 | 1971-06-15 | Verfahren zur Herstellung von 8-Alkoxy-3halogenmethyl-4-acetoxy- 10-methylen-2,9dioxatricyclo(43,l,03 7 )decanen |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2129507A1 DE2129507A1 (de) | 1972-12-21 |
| DE2129507B2 DE2129507B2 (de) | 1979-06-13 |
| DE2129507C3 true DE2129507C3 (de) | 1980-02-14 |
Family
ID=5810761
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712129507 Expired DE2129507C3 (de) | 1971-06-15 | 1971-06-15 | Verfahren zur Herstellung von 8-Alkoxy-3halogenmethyl-4-acetoxy- 10-methylen-2,9dioxatricyclo(43,l,03 7 )decanen |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS5538355B1 (OSRAM) |
| AT (1) | AT315869B (OSRAM) |
| CH (1) | CH572918A5 (OSRAM) |
| CS (1) | CS167350B2 (OSRAM) |
| DD (1) | DD99784A1 (OSRAM) |
| DE (1) | DE2129507C3 (OSRAM) |
| ES (1) | ES402726A1 (OSRAM) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2607106C2 (de) | 1976-02-21 | 1986-01-16 | Kali-Chemie Pharma Gmbh, 3000 Hannover | 2,9-Dioxatricyclo[4,3,1,0↑3↑↑,↑↑7↑]decane und Verfahren zu deren Herstellung |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI56533C (fi) * | 1973-02-08 | 1980-02-11 | Kali Chemie Pharma Gmbh | Saett att framstaella nya 4alfa-karbamyloxi-8-alkoxi-10-metylen-3-metyl-2,9-dioxatricyklo(4,3,1,03,7)-dekaner |
| DE2704621A1 (de) * | 1977-02-04 | 1978-08-10 | Kali Chemie Pharma Gmbh | 2,9-dioxatricyclo eckige klammer auf 4,3,1,0 hoch 3,7 eckige klammer zu decane und verfahren zu deren herstellung |
| DE2719916C2 (de) | 1977-05-04 | 1987-03-19 | Kali-Chemie Pharma Gmbh, 3000 Hannover | Verfahren zur Herstellung von 2,9-Dioxatricyclo[4,3,1,0↑3↑↑,↑↑7↑]decanen |
| DE3018635A1 (de) * | 1980-05-16 | 1981-11-26 | Celamerck Gmbh & Co Kg, 6507 Ingelheim | Verfahren zur herstellung von lineatin |
| DE3335827A1 (de) * | 1983-10-01 | 1985-04-18 | Kali-Chemie Pharma Gmbh, 3000 Hannover | Neue 2,6-dioxa-bicyclo-(2,2,2)-octan-7-yl- acetaldehyde |
| DE3335826A1 (de) * | 1983-10-01 | 1985-04-18 | Kali-Chemie Pharma Gmbh, 3000 Hannover | Neue n-(2,10-dioxa-tricyclo-(5,3,1,0(pfeil hoch)3(pfeil hoch)(pfeil hoch),(pfeil hoch)(pfeil hoch)8(pfeil hoch))- undecan-5-yl)-tryptamin-derivate |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE759840A (fr) * | 1969-12-08 | 1971-05-17 | Kali Chemie Ag | 2,9-dioxatricyclo-(4,3,1,0,3,7)-decanes et procede pour les preparer |
-
1971
- 1971-06-15 DE DE19712129507 patent/DE2129507C3/de not_active Expired
-
1972
- 1972-04-27 CH CH630072A patent/CH572918A5/xx not_active IP Right Cessation
- 1972-05-13 ES ES402726A patent/ES402726A1/es not_active Expired
- 1972-05-30 DD DD16329372A patent/DD99784A1/xx unknown
- 1972-06-07 CS CS394072A patent/CS167350B2/cs unknown
- 1972-06-08 JP JP5729172A patent/JPS5538355B1/ja active Pending
- 1972-06-14 AT AT511772A patent/AT315869B/de not_active IP Right Cessation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2607106C2 (de) | 1976-02-21 | 1986-01-16 | Kali-Chemie Pharma Gmbh, 3000 Hannover | 2,9-Dioxatricyclo[4,3,1,0↑3↑↑,↑↑7↑]decane und Verfahren zu deren Herstellung |
Also Published As
| Publication number | Publication date |
|---|---|
| CH572918A5 (OSRAM) | 1976-02-27 |
| JPS5538355B1 (OSRAM) | 1980-10-03 |
| DE2129507B2 (de) | 1979-06-13 |
| AT315869B (de) | 1974-06-10 |
| CS167350B2 (OSRAM) | 1976-04-29 |
| DE2129507A1 (de) | 1972-12-21 |
| DD99784A1 (OSRAM) | 1973-08-20 |
| ES402726A1 (es) | 1975-04-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) |