DE1793598C2 - 13-Alkyl-gona-1,3,5(10),8-tetraene. Ausscheidung aus: 1443123 - Google Patents
13-Alkyl-gona-1,3,5(10),8-tetraene. Ausscheidung aus: 1443123Info
- Publication number
- DE1793598C2 DE1793598C2 DE19611793598 DE1793598A DE1793598C2 DE 1793598 C2 DE1793598 C2 DE 1793598C2 DE 19611793598 DE19611793598 DE 19611793598 DE 1793598 A DE1793598 A DE 1793598A DE 1793598 C2 DE1793598 C2 DE 1793598C2
- Authority
- DE
- Germany
- Prior art keywords
- gona
- alkyl
- ecm
- tetraene
- eliminated
- 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
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- 230000008018 melting Effects 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- -1 ethylenedioxy group Chemical group 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 150000007659 semicarbazones Chemical class 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- 239000012279 sodium borohydride 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
- 230000017105 transposition Effects 0.000 description 2
- NJZGFUUVHQZZDR-UHFFFAOYSA-N 2-[6-(3-methoxyphenyl)-3-oxohexyl]-2-propylcyclopentane-1,3-dione Chemical compound C=1C=CC(OC)=CC=1CCCC(=O)CCC1(CCC)C(=O)CCC1=O NJZGFUUVHQZZDR-UHFFFAOYSA-N 0.000 description 1
- FSCAEMWIILOKLC-UHFFFAOYSA-N 2-propylcyclopentane-1,3-dione Chemical compound CCCC1C(=O)CCC1=O FSCAEMWIILOKLC-UHFFFAOYSA-N 0.000 description 1
- QBJXYRWUKSOXQY-UHFFFAOYSA-N 3-propyl-1,2-cyclopentanedione Chemical compound CCCC1CCC(=O)C1=O QBJXYRWUKSOXQY-UHFFFAOYSA-N 0.000 description 1
- QREBEZZOILCJEP-UHFFFAOYSA-N 6-(3-methoxyphenyl)hex-1-en-3-one Chemical compound COC1=CC=CC(CCCC(=O)C=C)=C1 QREBEZZOILCJEP-UHFFFAOYSA-N 0.000 description 1
- UJTTUOLQLCQZEA-UHFFFAOYSA-N 9h-fluoren-9-ylmethyl n-(4-hydroxybutyl)carbamate Chemical compound C1=CC=C2C(COC(=O)NCCCCO)C3=CC=CC=C3C2=C1 UJTTUOLQLCQZEA-UHFFFAOYSA-N 0.000 description 1
- QBDMUPIODGOVTP-UHFFFAOYSA-N CCCC1=CC=C[C]1 Chemical compound CCCC1=CC=C[C]1 QBDMUPIODGOVTP-UHFFFAOYSA-N 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
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- VTYYLEPIZMXCLO-UHFFFAOYSA-L calcium carbonate Substances [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000006210 cyclodehydration reaction Methods 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000000378 dietary effect Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000000926 separation method Methods 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
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006257 total synthesis reaction Methods 0.000 description 1
- 229960001124 trientine Drugs 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
- C07J1/0051—Estrane derivatives
- C07J1/0081—Substituted in position 17 alfa and 17 beta
- C07J1/0088—Substituted in position 17 alfa and 17 beta the substituent in position 17 alfa being an unsaturated hydrocarbon group
- C07J1/0096—Alkynyl derivatives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3267160A GB1010051A (en) | 1960-09-22 | 1960-09-22 | 13-alkyl steroids related to oestrone |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE1793598B1 DE1793598B1 (de) | 1972-05-31 |
| DE1793598C2 true DE1793598C2 (de) | 1973-01-04 |
Family
ID=10342265
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19611793598 Expired DE1793598C2 (de) | 1960-09-22 | 1961-09-19 | 13-Alkyl-gona-1,3,5(10),8-tetraene. Ausscheidung aus: 1443123 |
| DE19611668665 Pending DE1668665B1 (de) | 1960-09-22 | 1961-09-19 | Verfahren zur Herstellung von 13-Alkyl-gona-1,3,5(10)-trienen |
| DE19611443123 Pending DE1443123A1 (de) | 1960-09-22 | 1961-09-19 | Verfahren zur Herstellung von 13-Alkyl-gona-1,3,5(10)-trienen |
| DE19611793596 Expired DE1793596C3 (de) | 1960-09-22 | 1961-09-19 | 13-Alkyl-gona-l,3,(10)-triene. Ausscheidung aus: 1443123 |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19611668665 Pending DE1668665B1 (de) | 1960-09-22 | 1961-09-19 | Verfahren zur Herstellung von 13-Alkyl-gona-1,3,5(10)-trienen |
| DE19611443123 Pending DE1443123A1 (de) | 1960-09-22 | 1961-09-19 | Verfahren zur Herstellung von 13-Alkyl-gona-1,3,5(10)-trienen |
| DE19611793596 Expired DE1793596C3 (de) | 1960-09-22 | 1961-09-19 | 13-Alkyl-gona-l,3,(10)-triene. Ausscheidung aus: 1443123 |
Country Status (7)
| Country | Link |
|---|---|
| AT (2) | AT264728B (enExample) |
| CH (1) | CH417584A (enExample) |
| DE (4) | DE1793598C2 (enExample) |
| DK (1) | DK119159B (enExample) |
| GB (1) | GB1010051A (enExample) |
| IT (1) | IT1061783B (enExample) |
| SE (1) | SE308309B (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3549673A (en) * | 1967-03-09 | 1970-12-22 | Takeda Chemical Industries Ltd | Total synthesis of 13beta-substituted gonapolyen-17alpha-ols |
-
1960
- 1960-09-22 GB GB3267160A patent/GB1010051A/en not_active Expired
-
1961
- 1961-09-19 DE DE19611793598 patent/DE1793598C2/de not_active Expired
- 1961-09-19 DE DE19611668665 patent/DE1668665B1/de active Pending
- 1961-09-19 DE DE19611443123 patent/DE1443123A1/de active Pending
- 1961-09-19 DE DE19611793596 patent/DE1793596C3/de not_active Expired
- 1961-09-20 CH CH1093361A patent/CH417584A/de unknown
- 1961-09-20 AT AT712061A patent/AT264728B/de active
- 1961-09-20 AT AT07659/67A patent/AT281313B/de not_active IP Right Cessation
- 1961-09-21 DK DK375261A patent/DK119159B/da unknown
- 1961-09-22 IT IT1724661A patent/IT1061783B/it active
- 1961-09-22 SE SE942361A patent/SE308309B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SE308309B (enExample) | 1969-11-17 |
| AT264728B (de) | 1968-09-10 |
| GB1010051A (en) | 1965-11-17 |
| AT281313B (de) | 1970-05-25 |
| DE1793596B2 (de) | 1973-06-07 |
| DK119159B (da) | 1970-11-23 |
| DE1793596A1 (de) | 1972-06-08 |
| DE1793598B1 (de) | 1972-05-31 |
| IT1061783B (it) | 1983-04-30 |
| CH417584A (de) | 1966-07-31 |
| DE1793596C3 (de) | 1974-01-03 |
| DE1668665B1 (de) | 1972-05-04 |
| DE1443123A1 (de) | 1968-10-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| E77 | Valid patent as to the heymanns-index 1977 |