NO116143B - - Google Patents
Info
- Publication number
- NO116143B NO116143B NO160356A NO16035665A NO116143B NO 116143 B NO116143 B NO 116143B NO 160356 A NO160356 A NO 160356A NO 16035665 A NO16035665 A NO 16035665A NO 116143 B NO116143 B NO 116143B
- Authority
- NO
- Norway
- Prior art keywords
- acid
- reaction
- pseudo
- steroid
- molecule
- Prior art date
Links
- 238000006243 chemical reaction Methods 0.000 claims description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 11
- 150000002148 esters Chemical class 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 9
- 238000010438 heat treatment Methods 0.000 claims description 9
- -1 saturated aliphatic monocarboxylic acid Chemical class 0.000 claims description 9
- GMBQZIIUCVWOCD-WWASVFFGSA-N Sarsapogenine Chemical compound O([C@@H]1[C@@H]([C@]2(CC[C@@H]3[C@@]4(C)CC[C@H](O)C[C@H]4CC[C@H]3[C@@H]2C1)C)[C@@H]1C)[C@]11CC[C@H](C)CO1 GMBQZIIUCVWOCD-WWASVFFGSA-N 0.000 claims description 8
- QVZULXNXCIFMTL-IXCVKQQLSA-N 4802-74-8 Chemical compound O([C@@H]1[C@@H]([C@]2(CC(=O)[C@@H]3[C@@]4(C)CC[C@H](O)C[C@@H]4CC[C@H]3[C@@H]2C1)C)[C@@H]1C)[C@]11CC[C@@H](C)CO1 QVZULXNXCIFMTL-IXCVKQQLSA-N 0.000 claims description 7
- 239000003513 alkali Substances 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 150000001735 carboxylic acids Chemical class 0.000 claims description 7
- 238000001816 cooling Methods 0.000 claims description 7
- RTMWIZOXNKJHRE-UHFFFAOYSA-N Tigogenin Natural products CC1COC2CC(C)(OC12)C3CCC4C5CCC6CC(O)CCC6(C)C5CCC34C RTMWIZOXNKJHRE-UHFFFAOYSA-N 0.000 claims description 6
- 150000008064 anhydrides Chemical class 0.000 claims description 6
- WQLVFSAGQJTQCK-UHFFFAOYSA-N diosgenin Natural products CC1C(C2(CCC3C4(C)CCC(O)CC4=CCC3C2C2)C)C2OC11CCC(C)CO1 WQLVFSAGQJTQCK-UHFFFAOYSA-N 0.000 claims description 6
- 229960000583 acetic acid Drugs 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 4
- 239000007858 starting material Substances 0.000 claims description 4
- QOLRLLFJMZLYQJ-LOBDNJQFSA-N Hecogenin Chemical compound O([C@@H]1[C@@H]([C@]2(C(=O)C[C@@H]3[C@@]4(C)CC[C@H](O)C[C@@H]4CC[C@H]3[C@@H]2C1)C)[C@@H]1C)[C@]11CC[C@@H](C)CO1 QOLRLLFJMZLYQJ-LOBDNJQFSA-N 0.000 claims description 3
- OXLGJTRVVNGJRK-UHFFFAOYSA-N Hecogenin Natural products CC1CCC2(CC3CC4C5CCC6CC(O)CCC6(C)C5CC(=O)C4(C)C3C2C)OC1 OXLGJTRVVNGJRK-UHFFFAOYSA-N 0.000 claims description 3
- UVLDESQWQRMYKD-UHFFFAOYSA-N Neobotogenin Natural products CC1C(C2(C(=O)CC3C4(C)CCC(O)CC4=CCC3C2C2)C)C2OC11CCC(C)CO1 UVLDESQWQRMYKD-UHFFFAOYSA-N 0.000 claims description 3
- DWCSNWXARWMZTG-UHFFFAOYSA-N Trigonegenin A Natural products CC1C(C2(CCC3C4(C)CCC(O)C=C4CCC3C2C2)C)C2OC11CCC(C)CO1 DWCSNWXARWMZTG-UHFFFAOYSA-N 0.000 claims description 3
- WQLVFSAGQJTQCK-VKROHFNGSA-N diosgenin Chemical compound O([C@@H]1[C@@H]([C@]2(CC[C@@H]3[C@@]4(C)CC[C@H](O)CC4=CC[C@H]3[C@@H]2C1)C)[C@@H]1C)[C@]11CC[C@@H](C)CO1 WQLVFSAGQJTQCK-VKROHFNGSA-N 0.000 claims description 3
- 125000004423 acyloxy group Chemical group 0.000 claims description 2
- 230000007062 hydrolysis Effects 0.000 claims description 2
- 238000006460 hydrolysis reaction Methods 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 21
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 18
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
- 239000002253 acid Substances 0.000 description 16
- 238000010992 reflux Methods 0.000 description 14
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 150000003431 steroids Chemical class 0.000 description 10
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 description 7
- 150000007513 acids Chemical class 0.000 description 7
- 229960002446 octanoic acid Drugs 0.000 description 7
- 238000009835 boiling Methods 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- INLFWQCRAJUDCR-IQVMEADQSA-N (1R,2S,4S,5'S,6R,7S,8R,9S,12S,13S)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane] Chemical compound O([C@@H]1[C@@H]([C@]2(CC[C@@H]3[C@@]4(C)CCCCC4CC[C@H]3[C@@H]2C1)C)[C@@H]1C)[C@]11CC[C@H](C)CO1 INLFWQCRAJUDCR-IQVMEADQSA-N 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 5
- 150000008065 acid anhydrides Chemical class 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- FUFLCEKSBBHCMO-UHFFFAOYSA-N 11-dehydrocorticosterone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 FUFLCEKSBBHCMO-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- MFYSYFVPBJMHGN-ZPOLXVRWSA-N Cortisone Chemical compound O=C1CC[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 MFYSYFVPBJMHGN-ZPOLXVRWSA-N 0.000 description 3
- MFYSYFVPBJMHGN-UHFFFAOYSA-N Cortisone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)(O)C(=O)CO)C4C3CCC2=C1 MFYSYFVPBJMHGN-UHFFFAOYSA-N 0.000 description 3
- 230000015556 catabolic process Effects 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 229960004544 cortisone Drugs 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 238000006731 degradation reaction Methods 0.000 description 3
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- NWMIYTWHUDFRPL-UHFFFAOYSA-N sapogenin Natural products COC(=O)C1(CO)C(O)CCC2(C)C1CCC3(C)C2CC=C4C5C(C)(O)C(C)CCC5(CCC34C)C(=O)O NWMIYTWHUDFRPL-UHFFFAOYSA-N 0.000 description 3
- GMBQZIIUCVWOCD-UQHLGXRBSA-N (25R)-5beta-spirostan-3beta-ol Chemical compound O([C@@H]1[C@@H]([C@]2(CC[C@@H]3[C@@]4(C)CC[C@H](O)C[C@H]4CC[C@H]3[C@@H]2C1)C)[C@@H]1C)[C@]11CC[C@@H](C)CO1 GMBQZIIUCVWOCD-UQHLGXRBSA-N 0.000 description 2
- 125000004070 6 membered heterocyclic group Chemical group 0.000 description 2
- FLJFMDYYNMNASJ-UHFFFAOYSA-N 6-methyl-5,6-dihydrothieno[2,3-b]thiopyran-4-one Chemical compound S1C(C)CC(=O)C2=C1SC=C2 FLJFMDYYNMNASJ-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- 239000012259 ether extract Substances 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 229940088597 hormone Drugs 0.000 description 2
- 239000005556 hormone Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- RAFYDKXYXRZODZ-UHFFFAOYSA-N octanoyl octanoate Chemical compound CCCCCCCC(=O)OC(=O)CCCCCCC RAFYDKXYXRZODZ-UHFFFAOYSA-N 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000007127 saponification reaction Methods 0.000 description 2
- VUXXCVWHUXQPFJ-UHFFFAOYSA-N 1-methylsulfanyl-4-methylsulfinyl-6,7-dihydro-5h-cyclopenta[d]pyridazine Chemical compound CSC1=NN=C(S(C)=O)C2=C1CCC2 VUXXCVWHUXQPFJ-UHFFFAOYSA-N 0.000 description 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 description 1
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 1
- IQDKIMJGXXRZGR-UHFFFAOYSA-N Pseudotigogenin Natural products C1CC2CC(O)CCC2(C)C(CCC23C)C1C3CC1C2C(C)=C(CCC(CO)C)O1 IQDKIMJGXXRZGR-UHFFFAOYSA-N 0.000 description 1
- 241000220317 Rosa Species 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 239000006286 aqueous extract Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 229940117975 chromium trioxide Drugs 0.000 description 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
- GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000003163 gonadal steroid hormone Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- IQDKIMJGXXRZGR-HUEIYZRMSA-N pseudosmilagenin Chemical compound C([C@H]1CC2)[C@@H](O)CC[C@]1(C)[C@@H](CC[C@]13C)[C@@H]2[C@@H]3C[C@H]2[C@@H]1C(C)=C(CC[C@H](CO)C)O2 IQDKIMJGXXRZGR-HUEIYZRMSA-N 0.000 description 1
- IQDKIMJGXXRZGR-MEBFULDVSA-N pseudotigogenin Chemical compound C([C@@H]1CC2)[C@@H](O)CC[C@]1(C)[C@@H](CC[C@]13C)[C@@H]2[C@@H]3C[C@H]2[C@@H]1C(C)=C(CC[C@H](CO)C)O2 IQDKIMJGXXRZGR-MEBFULDVSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229950002323 smilagenin Drugs 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- G—PHYSICS
- G09—EDUCATION; CRYPTOGRAPHY; DISPLAY; ADVERTISING; SEALS
- G09B—EDUCATIONAL OR DEMONSTRATION APPLIANCES; APPLIANCES FOR TEACHING, OR COMMUNICATING WITH, THE BLIND, DEAF OR MUTE; MODELS; PLANETARIA; GLOBES; MAPS; DIAGRAMS
- G09B3/00—Manually or mechanically operated teaching appliances working with questions and answers
- G09B3/02—Manually or mechanically operated teaching appliances working with questions and answers of the type wherein the student is expected to construct an answer to the question which is presented or wherein the machine gives an answer to the question presented by a student
- G09B3/04—Manually or mechanically operated teaching appliances working with questions and answers of the type wherein the student is expected to construct an answer to the question which is presented or wherein the machine gives an answer to the question presented by a student of chart form
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41L—APPARATUS OR DEVICES FOR MANIFOLDING, DUPLICATING OR PRINTING FOR OFFICE OR OTHER COMMERCIAL PURPOSES; ADDRESSING MACHINES OR LIKE SERIES-PRINTING MACHINES
- B41L1/00—Devices for performing operations in connection with manifolding by means of pressure-sensitive layers or intermediaries, e.g. carbons; Accessories for manifolding purposes
- B41L1/20—Manifolding assemblies, e.g. book-like assemblies
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B42—BOOKBINDING; ALBUMS; FILES; SPECIAL PRINTED MATTER
- B42D—BOOKS; BOOK COVERS; LOOSE LEAVES; PRINTED MATTER CHARACTERISED BY IDENTIFICATION OR SECURITY FEATURES; PRINTED MATTER OF SPECIAL FORMAT OR STYLE NOT OTHERWISE PROVIDED FOR; DEVICES FOR USE THEREWITH AND NOT OTHERWISE PROVIDED FOR; MOVABLE-STRIP WRITING OR READING APPARATUS
- B42D19/00—Movable-strip writing or reading apparatus
Landscapes
- Engineering & Computer Science (AREA)
- Theoretical Computer Science (AREA)
- Physics & Mathematics (AREA)
- Educational Administration (AREA)
- Educational Technology (AREA)
- General Physics & Mathematics (AREA)
- Business, Economics & Management (AREA)
- Packaging Of Special Articles (AREA)
- Steroid Compounds (AREA)
- Toys (AREA)
- Management, Administration, Business Operations System, And Electronic Commerce (AREA)
- Folding Of Thin Sheet-Like Materials, Special Discharging Devices, And Others (AREA)
- Toilet Supplies (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DER39196A DE1254893B (de) | 1964-11-09 | 1964-11-09 | Aufgabenblatt mit Loesungskontrolle |
| DER40956A DE1295252B (de) | 1964-11-09 | 1965-06-26 | Aufgabenblatt |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO116143B true NO116143B (de) | 1969-02-03 |
Family
ID=25991837
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO160356A NO116143B (de) | 1964-11-09 | 1965-11-05 |
Country Status (10)
| Country | Link |
|---|---|
| BE (1) | BE671831A (de) |
| CH (2) | CH435822A (de) |
| DE (2) | DE1254893B (de) |
| DK (1) | DK117186B (de) |
| ES (1) | ES123092Y (de) |
| FI (1) | FI41696B (de) |
| GB (1) | GB1109650A (de) |
| NL (1) | NL6513680A (de) |
| NO (1) | NO116143B (de) |
| SE (1) | SE309868B (de) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3736006A (en) * | 1971-06-16 | 1973-05-29 | Polsky N | Envelope |
| JPS5524607Y2 (de) * | 1977-03-02 | 1980-06-12 | ||
| GB2125336B (en) * | 1982-08-17 | 1986-03-05 | Martin Brockley | Devices for making written records |
| CN108053723B (zh) * | 2017-11-24 | 2022-02-22 | 辽宁工业大学 | 一种英语翻译教学辅助装置 |
-
1964
- 1964-11-09 DE DER39196A patent/DE1254893B/de not_active Withdrawn
- 1964-11-09 CH CH1442064A patent/CH435822A/de unknown
-
1965
- 1965-06-26 DE DER40956A patent/DE1295252B/de not_active Withdrawn
- 1965-10-22 NL NL6513680A patent/NL6513680A/xx unknown
- 1965-10-26 GB GB45240/65A patent/GB1109650A/en not_active Expired
- 1965-11-03 FI FI2641/65A patent/FI41696B/fi active
- 1965-11-04 BE BE671831A patent/BE671831A/xx unknown
- 1965-11-05 SE SE14300/65A patent/SE309868B/xx unknown
- 1965-11-05 NO NO160356A patent/NO116143B/no unknown
- 1965-11-06 ES ES123092U patent/ES123092Y/es not_active Expired
- 1965-11-06 DK DK572265AA patent/DK117186B/da unknown
- 1965-12-20 CH CH1761165A patent/CH468049A/de unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK117186B (da) | 1970-03-23 |
| DE1295252B (de) | 1969-05-14 |
| SE309868B (de) | 1969-04-08 |
| ES123092U (es) | 1966-10-16 |
| ES123092Y (es) | 1967-08-01 |
| NL6513680A (de) | 1966-05-09 |
| CH468049A (de) | 1969-01-31 |
| BE671831A (de) | 1966-03-01 |
| CH435822A (de) | 1967-05-15 |
| DE1254893B (de) | 1967-11-23 |
| FI41696B (de) | 1969-09-30 |
| GB1109650A (en) | 1968-04-10 |
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