NO125926B - - Google Patents
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- Publication number
- NO125926B NO125926B NO163969A NO16396966A NO125926B NO 125926 B NO125926 B NO 125926B NO 163969 A NO163969 A NO 163969A NO 16396966 A NO16396966 A NO 16396966A NO 125926 B NO125926 B NO 125926B
- Authority
- NO
- Norway
- Prior art keywords
- parts
- weight
- propane
- acid
- sulfonic acid
- Prior art date
Links
- 238000000034 method Methods 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- -1 lower-alkylthio Chemical group 0.000 claims 4
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims 2
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 1
- UENWRTRMUIOCKN-UHFFFAOYSA-N benzyl thiol Chemical compound SCC1=CC=CC=C1 UENWRTRMUIOCKN-UHFFFAOYSA-N 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 238000011065 in-situ storage Methods 0.000 claims 1
- KOODSCBKXPPKHE-UHFFFAOYSA-N propanethioic s-acid Chemical compound CCC(S)=O KOODSCBKXPPKHE-UHFFFAOYSA-N 0.000 claims 1
- KOUKXHPPRFNWPP-UHFFFAOYSA-N pyrazine-2,5-dicarboxylic acid;hydrate Chemical compound O.OC(=O)C1=CN=C(C(O)=O)C=N1 KOUKXHPPRFNWPP-UHFFFAOYSA-N 0.000 claims 1
- 150000003431 steroids Chemical class 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 claims 1
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 43
- 150000003839 salts Chemical class 0.000 description 30
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 26
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000000203 mixture Substances 0.000 description 15
- 239000002253 acid Substances 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- FSSPGSAQUIYDCN-UHFFFAOYSA-N 1,3-Propane sultone Chemical compound O=S1(=O)CCCO1 FSSPGSAQUIYDCN-UHFFFAOYSA-N 0.000 description 12
- 239000011734 sodium Substances 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- 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 11
- 229910052708 sodium Inorganic materials 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
- 150000007513 acids Chemical class 0.000 description 9
- 235000011121 sodium hydroxide Nutrition 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- 125000000542 sulfonic acid group Chemical group 0.000 description 5
- 230000002152 alkylating effect Effects 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical class NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 4
- 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
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 229940100198 alkylating agent Drugs 0.000 description 3
- 239000002168 alkylating agent Substances 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 3
- 229940073608 benzyl chloride Drugs 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 238000005260 corrosion Methods 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- MHYFEEDKONKGEB-UHFFFAOYSA-N oxathiane 2,2-dioxide Chemical compound O=S1(=O)CCCCO1 MHYFEEDKONKGEB-UHFFFAOYSA-N 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- BIYKKPCIHIHZHB-UHFFFAOYSA-N 1-amino-4-phenylbutane-1-sulfonic acid Chemical compound C(C1=CC=CC=C1)CCC(S(=O)(=O)O)N BIYKKPCIHIHZHB-UHFFFAOYSA-N 0.000 description 2
- CPPHSWZWNSTFGV-UHFFFAOYSA-N 3-(benzylamino)propane-1-sulfonic acid Chemical compound OS(=O)(=O)CCCNCC1=CC=CC=C1 CPPHSWZWNSTFGV-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical compound S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 230000009965 odorless effect Effects 0.000 description 2
- FMJAECNDSRNBCU-UHFFFAOYSA-N 1-amino-3-cyclohexylpropane-1-sulfonic acid Chemical compound OS(=O)(=O)C(N)CCC1CCCCC1 FMJAECNDSRNBCU-UHFFFAOYSA-N 0.000 description 1
- IBPKDFDXRUCNOG-UHFFFAOYSA-N 1-amino-4-cyclohexylbutane-1-sulfonic acid Chemical compound OS(=O)(=O)C(N)CCCC1CCCCC1 IBPKDFDXRUCNOG-UHFFFAOYSA-N 0.000 description 1
- BVJHPLDMZKSTIL-UHFFFAOYSA-N 1-aminoheptane-1-sulfonic acid Chemical compound CCCCCCC(N)S(O)(=O)=O BVJHPLDMZKSTIL-UHFFFAOYSA-N 0.000 description 1
- MMLZJBSKXRPCLK-UHFFFAOYSA-N 1-aminohexane-1-sulfonic acid Chemical compound CCCCCC(N)S(O)(=O)=O MMLZJBSKXRPCLK-UHFFFAOYSA-N 0.000 description 1
- GMPYNOTVKNXELU-UHFFFAOYSA-N 1-bromoethanesulfonic acid Chemical compound CC(Br)S(O)(=O)=O GMPYNOTVKNXELU-UHFFFAOYSA-N 0.000 description 1
- SGSMPWTZYGTIEA-UHFFFAOYSA-N 2-(ethylamino)ethanesulfonic acid Chemical compound CCNCCS(O)(=O)=O SGSMPWTZYGTIEA-UHFFFAOYSA-N 0.000 description 1
- ZDSCFBCGDDCJFZ-UHFFFAOYSA-N 2-(methylamino)ethanesulfonic acid;sodium Chemical compound [Na].CNCCS(O)(=O)=O ZDSCFBCGDDCJFZ-UHFFFAOYSA-N 0.000 description 1
- ZZVWIMPMMGCOMR-UHFFFAOYSA-N 3-(butylamino)propane-1-sulfonic acid Chemical compound CCCCNCCCS(O)(=O)=O ZZVWIMPMMGCOMR-UHFFFAOYSA-N 0.000 description 1
- RPKWNMFDAOACCX-UHFFFAOYSA-N 4-chloro-3-nitrobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(Cl)C([N+]([O-])=O)=C1 RPKWNMFDAOACCX-UHFFFAOYSA-N 0.000 description 1
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 description 1
- PJWWRFATQTVXHA-UHFFFAOYSA-N Cyclohexylaminopropanesulfonic acid Chemical compound OS(=O)(=O)CCCNC1CCCCC1 PJWWRFATQTVXHA-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- UCLTVQRWNVIZTL-UHFFFAOYSA-N benzyl n-butylcarbamodithioate Chemical compound CCCCNC(=S)SCC1=CC=CC=C1 UCLTVQRWNVIZTL-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000000571 coke Substances 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 229940008406 diethyl sulfate Drugs 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 235000019439 ethyl acetate Nutrition 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical class NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- 150000003459 sulfonic acid esters Chemical class 0.000 description 1
- 150000008053 sultones Chemical class 0.000 description 1
- 238000004073 vulcanization Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J75/00—Processes for the preparation of steroids in general
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 (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1007465A CH481086A (de) | 1965-07-19 | 1965-07-19 | Verfahren zur Herstellung von neuen 9B,10 -Steroiden |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO125926B true NO125926B (nl) | 1972-11-27 |
Family
ID=4359045
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO163969A NO125926B (nl) | 1965-07-19 | 1966-07-18 |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US3409642A (nl) |
| AT (2) | AT273389B (nl) |
| BE (1) | BE684186A (nl) |
| BR (1) | BR6681347D0 (nl) |
| CH (1) | CH481086A (nl) |
| DE (1) | DE1568771A1 (nl) |
| DK (1) | DK116734B (nl) |
| ES (1) | ES329219A1 (nl) |
| FI (1) | FI45445C (nl) |
| FR (2) | FR7189M (nl) |
| GB (1) | GB1101129A (nl) |
| IL (1) | IL26159A (nl) |
| NL (1) | NL6610092A (nl) |
| NO (1) | NO125926B (nl) |
| SE (1) | SE340274B (nl) |
| YU (1) | YU31199B (nl) |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2875215A (en) * | 1957-05-24 | 1959-02-24 | Searle & Co | 1-acylthio substitution products of 3, 17-dioxygenated androstane derivatives |
| US3198792A (en) * | 1962-06-12 | 1965-08-03 | Philips Corp | 10alpha methyl, 9beta hormonal steroids |
-
1965
- 1965-07-19 CH CH1007465A patent/CH481086A/de not_active IP Right Cessation
-
1966
- 1966-07-08 DE DE19661568771 patent/DE1568771A1/de active Pending
- 1966-07-13 AT AT671866A patent/AT273389B/de active
- 1966-07-13 AT AT01573/68A patent/AT277482B/de active
- 1966-07-14 US US565110A patent/US3409642A/en not_active Expired - Lifetime
- 1966-07-15 BE BE684186D patent/BE684186A/xx unknown
- 1966-07-16 ES ES0329219A patent/ES329219A1/es not_active Expired
- 1966-07-17 IL IL26159A patent/IL26159A/en unknown
- 1966-07-18 NL NL6610092A patent/NL6610092A/xx unknown
- 1966-07-18 FR FR69669A patent/FR7189M/fr not_active Expired
- 1966-07-18 BR BR181347/66A patent/BR6681347D0/pt unknown
- 1966-07-18 NO NO163969A patent/NO125926B/no unknown
- 1966-07-18 YU YU1371/66A patent/YU31199B/xx unknown
- 1966-07-18 GB GB32210/66A patent/GB1101129A/en not_active Expired
- 1966-07-18 SE SE09785/66A patent/SE340274B/xx unknown
- 1966-07-19 FR FR69807A patent/FR1500909A/fr not_active Expired
- 1966-07-19 FI FI661931A patent/FI45445C/fi active
- 1966-07-19 DK DK373666AA patent/DK116734B/da unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US3409642A (en) | 1968-11-05 |
| DE1568771A1 (de) | 1970-04-30 |
| AT277482B (de) | 1969-12-29 |
| FI45445C (fi) | 1972-06-12 |
| GB1101129A (en) | 1968-01-31 |
| ES329219A1 (es) | 1967-08-16 |
| NL6610092A (nl) | 1967-01-20 |
| FR7189M (nl) | 1969-08-18 |
| CH481086A (de) | 1969-11-15 |
| IL26159A (en) | 1970-02-19 |
| YU31199B (en) | 1973-02-28 |
| SE340274B (nl) | 1971-11-15 |
| FI45445B (nl) | 1972-02-29 |
| BE684186A (nl) | 1967-01-16 |
| FR1500909A (fr) | 1967-11-10 |
| AT273389B (de) | 1969-08-11 |
| DK116734B (da) | 1970-02-09 |
| BR6681347D0 (pt) | 1973-12-26 |
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