FI57928C - Nya saosom mellanprodukter vid framstaellning av steroidhormoner anvaendbara bicykloalkanderivat och foerfarande foer deras framstaellning - Google Patents
Nya saosom mellanprodukter vid framstaellning av steroidhormoner anvaendbara bicykloalkanderivat och foerfarande foer deras framstaellning Download PDFInfo
- Publication number
- FI57928C FI57928C FI3647/72A FI364772A FI57928C FI 57928 C FI57928 C FI 57928C FI 3647/72 A FI3647/72 A FI 3647/72A FI 364772 A FI364772 A FI 364772A FI 57928 C FI57928 C FI 57928C
- Authority
- FI
- Finland
- Prior art keywords
- methyl
- tetrahydroindan
- framstaellning
- dissolved
- tert
- Prior art date
Links
- -1 hydroxymethylene group Chemical group 0.000 claims description 32
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 17
- 238000002360 preparation method Methods 0.000 claims description 7
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- BUUPQKDIAURBJP-UHFFFAOYSA-N sulfinic acid Chemical compound OS=O BUUPQKDIAURBJP-UHFFFAOYSA-N 0.000 claims description 6
- 239000000543 intermediate Substances 0.000 claims description 5
- 150000003512 tertiary amines Chemical class 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 239000003270 steroid hormone Substances 0.000 claims description 4
- 150000003457 sulfones Chemical class 0.000 claims description 4
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- 150000003568 thioethers Chemical class 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
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- 239000000243 solution Substances 0.000 description 22
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- 230000007935 neutral effect Effects 0.000 description 4
- VIKNJXKGJWUCNN-XGXHKTLJSA-N norethisterone Chemical compound O=C1CC[C@@H]2[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 VIKNJXKGJWUCNN-XGXHKTLJSA-N 0.000 description 4
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- 235000011152 sodium sulphate Nutrition 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
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- PMBXCGGQNSVESQ-UHFFFAOYSA-N 1-Hexanethiol Chemical compound CCCCCCS PMBXCGGQNSVESQ-UHFFFAOYSA-N 0.000 description 3
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- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- DSICTTBMRSZYJL-UHFFFAOYSA-N ethyl n,n-dibutylcarbamate Chemical compound CCCCN(CCCC)C(=O)OCC DSICTTBMRSZYJL-UHFFFAOYSA-N 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000008098 formaldehyde solution Substances 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
- 150000002366 halogen compounds Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- VOIGMFQJDZTEKW-UHFFFAOYSA-N hexane-3-thiol Chemical compound CCCC(S)CC VOIGMFQJDZTEKW-UHFFFAOYSA-N 0.000 description 1
- UMRWDRULUZVLAY-UHFFFAOYSA-N hydroxymethylsulfonylmethanol Chemical compound OCS(=O)(=O)CO UMRWDRULUZVLAY-UHFFFAOYSA-N 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 229960004719 nandrolone Drugs 0.000 description 1
- ZDHCJEIGTNNEMY-XGXHKTLJSA-N norethandrolone Chemical compound C1CC2=CC(=O)CC[C@@H]2[C@@H]2[C@@H]1[C@@H]1CC[C@](CC)(O)[C@@]1(C)CC2 ZDHCJEIGTNNEMY-XGXHKTLJSA-N 0.000 description 1
- 229940053934 norethindrone Drugs 0.000 description 1
- 229960001652 norethindrone acetate Drugs 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 235000021395 porridge Nutrition 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 238000003918 potentiometric titration Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000004053 quinones Chemical class 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003455 sulfinic acids Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003509 tertiary alcohols Chemical class 0.000 description 1
- LWRYDHOHXNQTSK-UHFFFAOYSA-N thiophene oxide Chemical compound O=S1C=CC=C1 LWRYDHOHXNQTSK-UHFFFAOYSA-N 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C321/00—Thiols, sulfides, hydropolysulfides or polysulfides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
-
- 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
- C07D317/10—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 not condensed with other rings
- C07D317/14—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 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/30—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
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
- C07D319/06—1,3-Dioxanes; Hydrogenated 1,3-dioxanes not condensed with other rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2165320 | 1971-12-24 | ||
| DE2165320A DE2165320C2 (de) | 1971-12-24 | 1971-12-24 | Verfahren zur Herstellung von Bicycloalkan-thio-Derivaten |
| DE2221704 | 1972-04-29 | ||
| DE19722221704 DE2221704A1 (de) | 1972-04-29 | 1972-04-29 | Neue bicycloalkan-derivate und ihre herstellung |
| DE2254175 | 1972-11-02 | ||
| DE2254175A DE2254175A1 (de) | 1972-11-02 | 1972-11-02 | Neue 9,10-seco-oestran-derivate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FI57928B FI57928B (fi) | 1980-07-31 |
| FI57928C true FI57928C (fi) | 1980-11-10 |
Family
ID=27183968
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI3647/72A FI57928C (fi) | 1971-12-24 | 1972-12-22 | Nya saosom mellanprodukter vid framstaellning av steroidhormoner anvaendbara bicykloalkanderivat och foerfarande foer deras framstaellning |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US4008253A (xx) |
| AR (1) | AR200121A1 (xx) |
| AT (1) | AT326625B (xx) |
| BE (1) | BE793252A (xx) |
| CH (1) | CH576434A5 (xx) |
| CS (1) | CS186217B2 (xx) |
| DD (1) | DD105439A5 (xx) |
| DK (1) | DK141166C (xx) |
| ES (1) | ES409966A1 (xx) |
| FI (1) | FI57928C (xx) |
| FR (1) | FR2169856A1 (xx) |
| GB (2) | GB1419630A (xx) |
| HU (1) | HU167383B (xx) |
| IE (1) | IE37023B1 (xx) |
| IL (1) | IL41155A (xx) |
| NL (1) | NL7217629A (xx) |
| SE (1) | SE411344B (xx) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4045490A (en) * | 1973-12-21 | 1977-08-30 | Hoffmann-La Roche Inc. | 9,10-Seco-steroid preparation |
| US4064173A (en) * | 1973-12-21 | 1977-12-20 | Hoffmann-La Roche, Inc. | 9,10-Seco-steroids |
| DE2449031C2 (de) * | 1974-10-11 | 1983-08-04 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | Verfahren zur Herstellung von 13β-Alkyl-4-gonen-3,17-dionen |
| CH614219A5 (en) * | 1975-04-21 | 1979-11-15 | Hoffmann La Roche | Process for the preparation of D-homosteroids |
| DE2832606A1 (de) * | 1978-07-21 | 1980-01-31 | Schering Ag | Verfahren zur herstellung von 7 alpha -methyl-oestrogenen |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR96536E (fr) * | 1967-12-04 | 1972-10-20 | Hoffmann La Roche | Procédé pour la préparation de benzindenes. |
-
0
- BE BE793252D patent/BE793252A/xx unknown
-
1972
- 1972-12-14 CH CH1820672A patent/CH576434A5/xx not_active IP Right Cessation
- 1972-12-19 IE IE1773/72A patent/IE37023B1/xx unknown
- 1972-12-19 DK DK634572A patent/DK141166C/da active
- 1972-12-20 CS CS7200008800A patent/CS186217B2/cs unknown
- 1972-12-21 GB GB3476975A patent/GB1419630A/en not_active Expired
- 1972-12-21 GB GB5923972A patent/GB1419629A/en not_active Expired
- 1972-12-21 DD DD167799A patent/DD105439A5/xx unknown
- 1972-12-22 AR AR245821A patent/AR200121A1/es active
- 1972-12-22 US US05/317,549 patent/US4008253A/en not_active Expired - Lifetime
- 1972-12-22 ES ES409966A patent/ES409966A1/es not_active Expired
- 1972-12-22 FI FI3647/72A patent/FI57928C/fi active
- 1972-12-22 SE SE7216910A patent/SE411344B/xx unknown
- 1972-12-22 HU HUSCHE419*1A patent/HU167383B/hu unknown
- 1972-12-23 NL NL7217629A patent/NL7217629A/xx not_active Application Discontinuation
- 1972-12-24 IL IL41155A patent/IL41155A/en unknown
- 1972-12-26 FR FR7246152A patent/FR2169856A1/fr not_active Withdrawn
-
1974
- 1974-04-12 AT AT310574*7A patent/AT326625B/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| AT326625B (de) | 1975-12-29 |
| BE793252A (fr) | 1973-06-22 |
| FI57928B (fi) | 1980-07-31 |
| IL41155A0 (en) | 1973-02-28 |
| IE37023L (en) | 1973-06-24 |
| IE37023B1 (en) | 1977-04-13 |
| DK141166C (da) | 1980-07-07 |
| AR200121A1 (es) | 1974-10-24 |
| NL7217629A (xx) | 1973-06-26 |
| GB1419630A (en) | 1975-12-31 |
| GB1419629A (en) | 1975-12-31 |
| FR2169856A1 (xx) | 1973-09-14 |
| DK141166B (da) | 1980-01-28 |
| CH576434A5 (xx) | 1976-06-15 |
| CS186217B2 (en) | 1978-11-30 |
| ES409966A1 (es) | 1976-04-16 |
| HU167383B (xx) | 1975-09-27 |
| US4008253A (en) | 1977-02-15 |
| ATA310574A (de) | 1975-03-15 |
| SE411344B (sv) | 1979-12-17 |
| DD105439A5 (xx) | 1974-04-20 |
| IL41155A (en) | 1976-07-30 |
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