FI67859C - Foerfarande foer framstaellning av pregnen-21-tioestrar - Google Patents
Foerfarande foer framstaellning av pregnen-21-tioestrar Download PDFInfo
- Publication number
- FI67859C FI67859C FI793683A FI793683A FI67859C FI 67859 C FI67859 C FI 67859C FI 793683 A FI793683 A FI 793683A FI 793683 A FI793683 A FI 793683A FI 67859 C FI67859 C FI 67859C
- Authority
- FI
- Finland
- Prior art keywords
- formula
- hydrogen
- color
- alkyl
- fluorine
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 49
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 48
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
- 239000000725 suspension Substances 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 238000006277 sulfonation reaction Methods 0.000 claims description 12
- 239000003795 chemical substances by application Substances 0.000 claims description 11
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- 239000011737 fluorine Substances 0.000 claims description 7
- -1 steroid radical Chemical class 0.000 claims description 7
- 229910052783 alkali metal Inorganic materials 0.000 claims description 6
- 150000001340 alkali metals Chemical class 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 239000012429 reaction media Substances 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 150000003973 alkyl amines Chemical class 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- OPFJDXRVMFKJJO-ZHHKINOHSA-N N-{[3-(2-benzamido-4-methyl-1,3-thiazol-5-yl)-pyrazol-5-yl]carbonyl}-G-dR-G-dD-dD-dD-NH2 Chemical compound S1C(C=2NN=C(C=2)C(=O)NCC(=O)N[C@H](CCCN=C(N)N)C(=O)NCC(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(N)=O)=C(C)N=C1NC(=O)C1=CC=CC=C1 OPFJDXRVMFKJJO-ZHHKINOHSA-N 0.000 claims 1
- 210000001217 buttock Anatomy 0.000 claims 1
- 229940126086 compound 21 Drugs 0.000 claims 1
- 230000008014 freezing Effects 0.000 claims 1
- 238000007710 freezing Methods 0.000 claims 1
- 230000001939 inductive effect Effects 0.000 claims 1
- 239000000243 solution Substances 0.000 description 26
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- 239000002253 acid Substances 0.000 description 16
- 239000000047 product Substances 0.000 description 11
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- 239000002516 radical scavenger Substances 0.000 description 6
- 125000005270 trialkylamine group Chemical group 0.000 description 6
- 229940086542 triethylamine Drugs 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 5
- 239000012535 impurity Substances 0.000 description 5
- 239000000543 intermediate Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- LLCOIQRNSJBFSN-UHFFFAOYSA-N methane;sulfurochloridic acid Chemical group C.OS(Cl)(=O)=O LLCOIQRNSJBFSN-UHFFFAOYSA-N 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 150000003431 steroids Chemical class 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- 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 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 159000000032 aromatic acids Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 2
- 239000002198 insoluble material Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- YJESALUAHUVISI-UHFFFAOYSA-N 3,5-dimethylhexan-2-one Chemical compound CC(C)CC(C)C(C)=O YJESALUAHUVISI-UHFFFAOYSA-N 0.000 description 1
- LBVWMBBKFFQMRX-UHFFFAOYSA-N 4-chlorobenzenecarbothioic s-acid Chemical compound SC(=O)C1=CC=C(Cl)C=C1 LBVWMBBKFFQMRX-UHFFFAOYSA-N 0.000 description 1
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- WLJXESLORBMHBD-UHFFFAOYSA-O CCCC(O)=[S+]CC Chemical compound CCCC(O)=[S+]CC WLJXESLORBMHBD-UHFFFAOYSA-O 0.000 description 1
- HTEDURXHGBDPRO-QYYRQDGDSA-N C[C@@H]1C[C@H]2[C@@H]3CC(C4=CC(=O)C=C[C@@]4([C@H]3CC[C@@]2([C@H]1C(=O)C)C)C)F Chemical compound C[C@@H]1C[C@H]2[C@@H]3CC(C4=CC(=O)C=C[C@@]4([C@H]3CC[C@@]2([C@H]1C(=O)C)C)C)F HTEDURXHGBDPRO-QYYRQDGDSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229960000250 adipic acid Drugs 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 239000003637 basic solution Substances 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- IZDROVVXIHRYMH-UHFFFAOYSA-N methanesulfonic anhydride Chemical compound CS(=O)(=O)OS(C)(=O)=O IZDROVVXIHRYMH-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- HNPPKZRZKDKXDO-UHFFFAOYSA-N n,n-dimethylformamide;propan-2-one Chemical compound CC(C)=O.CN(C)C=O HNPPKZRZKDKXDO-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000003128 pregnanes Chemical class 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 150000007970 thio esters Chemical class 0.000 description 1
- BISFDZNIUZIKJD-XDANTLIUSA-N tixocortol pivalate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)CSC(=O)C(C)(C)C)(O)[C@@]1(C)C[C@@H]2O BISFDZNIUZIKJD-XDANTLIUSA-N 0.000 description 1
- 125000005490 tosylate group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J31/00—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring
- C07J31/006—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring not covered by C07J31/003
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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7833959A FR2442856A1 (fr) | 1978-12-01 | 1978-12-01 | Procede de preparation de steroides |
| FR7833959 | 1978-12-01 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI793683A7 FI793683A7 (fi) | 1980-06-02 |
| FI67859B FI67859B (fi) | 1985-02-28 |
| FI67859C true FI67859C (fi) | 1985-06-10 |
Family
ID=9215594
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI793683A FI67859C (fi) | 1978-12-01 | 1979-11-23 | Foerfarande foer framstaellning av pregnen-21-tioestrar |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US4269778A (da) |
| JP (1) | JPS5858359B2 (da) |
| AT (1) | AT370740B (da) |
| AU (1) | AU526109B2 (da) |
| BE (1) | BE880343A (da) |
| CA (1) | CA1124711A (da) |
| CH (1) | CH648329A5 (da) |
| DE (1) | DE2948142C2 (da) |
| DK (1) | DK160281C (da) |
| ES (1) | ES486325A1 (da) |
| FI (1) | FI67859C (da) |
| FR (1) | FR2442856A1 (da) |
| GB (1) | GB2037290B (da) |
| GR (1) | GR63585B (da) |
| HU (1) | HU180951B (da) |
| IL (1) | IL58778A (da) |
| IT (1) | IT1124356B (da) |
| NL (1) | NL7908634A (da) |
| PT (1) | PT70458A (da) |
| SE (1) | SE441833B (da) |
| YU (1) | YU40766B (da) |
| ZA (1) | ZA796226B (da) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2510582B1 (fr) * | 1981-07-30 | 1986-05-30 | Sipsy | Steroides esterifies en la position 17 et thio-esterifies en la position 21, leur procede de preparation et leur application comme medicament |
| FR2529894B2 (fr) * | 1981-07-30 | 1986-07-25 | Jouveinal | Steroides esterifies en la position 17 et thio-esterifies en la position 21 et leur application comme medicament |
| FI80790C (fi) * | 1988-02-22 | 1990-07-10 | Matti Henttinen | Foerfarande och anordning foer bestaemning av ett spaors laege. |
| US5439901A (en) * | 1993-07-23 | 1995-08-08 | The Procter & Gamble Company | Cyproterone thiopivalate |
| US5344651A (en) * | 1993-07-23 | 1994-09-06 | The Procter & Gamble Company | Cyproterone acetate thioacetate |
| IES960231A2 (en) * | 1996-03-20 | 1996-07-24 | Losbanos Ltd | Manufacture of steroids |
| ES2716401T3 (es) * | 2013-09-25 | 2019-06-12 | H4 Pharma | Procedimiento de síntesis de una sal mineral del ácido piválico como producto intermedio |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1187M (fr) * | 1961-03-17 | 1962-03-19 | Roussel Uclaf | Nouveau médicament notamment pour le traitement des manifestations inflammatoires d'origine rhumatismale arthritique ou infectieuse. |
| CH566349A5 (da) * | 1969-12-24 | 1975-09-15 | Ciba Geigy Ag | |
| US3803133A (en) * | 1972-12-15 | 1974-04-09 | Squibb & Sons Inc | 21-sulfinyl steroids |
| FR2231374B1 (da) * | 1973-05-30 | 1976-10-22 | Jouveinal Sa |
-
1978
- 1978-12-01 FR FR7833959A patent/FR2442856A1/fr active Granted
-
1979
- 1979-11-15 PT PT70458A patent/PT70458A/pt unknown
- 1979-11-19 ZA ZA00796226A patent/ZA796226B/xx unknown
- 1979-11-20 US US06/096,153 patent/US4269778A/en not_active Expired - Lifetime
- 1979-11-22 AU AU53116/79A patent/AU526109B2/en not_active Expired
- 1979-11-22 GR GR60575A patent/GR63585B/el unknown
- 1979-11-22 IL IL58778A patent/IL58778A/xx unknown
- 1979-11-23 FI FI793683A patent/FI67859C/fi not_active IP Right Cessation
- 1979-11-23 IT IT12840/79A patent/IT1124356B/it active
- 1979-11-26 ES ES486325A patent/ES486325A1/es not_active Expired
- 1979-11-27 YU YU2901/79A patent/YU40766B/xx unknown
- 1979-11-28 NL NL7908634A patent/NL7908634A/nl active Search and Examination
- 1979-11-29 DE DE2948142A patent/DE2948142C2/de not_active Expired
- 1979-11-29 BE BE6/47023A patent/BE880343A/fr not_active IP Right Cessation
- 1979-11-29 SE SE7909852A patent/SE441833B/sv not_active IP Right Cessation
- 1979-11-29 CH CH10632/79A patent/CH648329A5/fr not_active IP Right Cessation
- 1979-11-30 CA CA340,967A patent/CA1124711A/en not_active Expired
- 1979-11-30 AT AT0760479A patent/AT370740B/de not_active IP Right Cessation
- 1979-11-30 HU HU79SI1732A patent/HU180951B/hu unknown
- 1979-11-30 GB GB7941360A patent/GB2037290B/en not_active Expired
- 1979-11-30 DK DK511279A patent/DK160281C/da active
- 1979-12-01 JP JP54154995A patent/JPS5858359B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DK160281B (da) | 1991-02-18 |
| FR2442856A1 (fr) | 1980-06-27 |
| GB2037290B (en) | 1983-02-09 |
| AU5311679A (en) | 1980-06-05 |
| BE880343A (fr) | 1980-05-29 |
| IT7912840A0 (it) | 1979-11-23 |
| DE2948142A1 (de) | 1980-06-04 |
| GR63585B (en) | 1979-11-23 |
| FI67859B (fi) | 1985-02-28 |
| NL7908634A (nl) | 1980-06-03 |
| YU290179A (en) | 1983-01-21 |
| GB2037290A (en) | 1980-07-09 |
| IL58778A0 (en) | 1980-02-29 |
| US4269778A (en) | 1981-05-26 |
| ZA796226B (en) | 1981-06-24 |
| DK160281C (da) | 1991-07-29 |
| DK511279A (da) | 1980-06-02 |
| JPS5579399A (en) | 1980-06-14 |
| ES486325A1 (es) | 1980-06-16 |
| FI793683A7 (fi) | 1980-06-02 |
| AT370740B (de) | 1983-04-25 |
| YU40766B (en) | 1986-06-30 |
| SE441833B (sv) | 1985-11-11 |
| CH648329A5 (fr) | 1985-03-15 |
| ATA760479A (de) | 1982-09-15 |
| IL58778A (en) | 1982-11-30 |
| AU526109B2 (en) | 1982-12-16 |
| PT70458A (fr) | 1979-12-01 |
| FR2442856B1 (da) | 1981-05-22 |
| IT1124356B (it) | 1986-05-07 |
| CA1124711A (en) | 1982-06-01 |
| HU180951B (en) | 1983-05-30 |
| SE7909852L (sv) | 1980-06-02 |
| DE2948142C2 (de) | 1982-06-24 |
| JPS5858359B2 (ja) | 1983-12-24 |
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