NO124646B - - Google Patents
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- Publication number
- NO124646B NO124646B NO164596A NO16459666A NO124646B NO 124646 B NO124646 B NO 124646B NO 164596 A NO164596 A NO 164596A NO 16459666 A NO16459666 A NO 16459666A NO 124646 B NO124646 B NO 124646B
- Authority
- NO
- Norway
- Prior art keywords
- allopregnen
- carboxylic acid
- dione
- group
- double bond
- Prior art date
Links
- 238000000034 method Methods 0.000 claims description 7
- 125000004043 oxo group Chemical group O=* 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 239000012467 final product Substances 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000012299 nitrogen atmosphere Substances 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- 239000012362 glacial acetic acid Substances 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 150000003431 steroids Chemical class 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 1
- YCURDTPXHPXCKH-UHFFFAOYSA-N 2-ethylbutanoyl 2-ethylbutanoate Chemical compound CCC(CC)C(=O)OC(=O)C(CC)CC YCURDTPXHPXCKH-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-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
- WVVOBOZHTQJXPB-UHFFFAOYSA-N N-anilino-N-nitronitramide Chemical compound [N+](=O)([O-])N(NC1=CC=CC=C1)[N+](=O)[O-] WVVOBOZHTQJXPB-UHFFFAOYSA-N 0.000 description 1
- ORNBQBCIOKFOEO-YQUGOWONSA-N Pregnenolone Natural products O=C(C)[C@@H]1[C@@]2(C)[C@H]([C@H]3[C@@H]([C@]4(C)C(=CC3)C[C@@H](O)CC4)CC2)CC1 ORNBQBCIOKFOEO-YQUGOWONSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000002456 anti-arthritic effect Effects 0.000 description 1
- 238000009835 boiling Methods 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
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- -1 diethyl acetate Chemical compound 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- PKHMTIRCAFTBDS-UHFFFAOYSA-N hexanoyl hexanoate Chemical compound CCCCCC(=O)OC(=O)CCCCC PKHMTIRCAFTBDS-UHFFFAOYSA-N 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 229960000249 pregnenolone Drugs 0.000 description 1
- OZZAYJQNMKMUSD-DMISRAGPSA-N pregnenolone succinate Chemical compound C1C=C2C[C@@H](OC(=O)CCC(O)=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 OZZAYJQNMKMUSD-DMISRAGPSA-N 0.000 description 1
- 230000001072 progestational effect Effects 0.000 description 1
- 229960003387 progesterone Drugs 0.000 description 1
- 239000000186 progesterone Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L25/00—Compositions of, homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring; Compositions of derivatives of such polymers
- C08L25/02—Homopolymers or copolymers of hydrocarbons
- C08L25/04—Homopolymers or copolymers of styrene
- C08L25/06—Polystyrene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L53/00—Compositions of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L53/00—Compositions of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
- C08L53/02—Compositions of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers of vinyl-aromatic monomers and conjugated dienes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L9/00—Compositions of homopolymers or copolymers of conjugated diene hydrocarbons
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Graft Or Block Polymers (AREA)
- Bag Frames (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US48562565A | 1965-09-07 | 1965-09-07 | |
| US51878366A | 1966-01-05 | 1966-01-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO124646B true NO124646B (sv) | 1972-05-15 |
Family
ID=27048424
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO164596A NO124646B (sv) | 1965-09-07 | 1966-09-07 | |
| NO00011/71A NO127619B (sv) | 1965-09-07 | 1971-01-04 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO00011/71A NO127619B (sv) | 1965-09-07 | 1971-01-04 |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US3429951A (sv) |
| BE (1) | BE686558A (sv) |
| DE (1) | DE1694749B2 (sv) |
| DK (1) | DK112898B (sv) |
| ES (1) | ES330671A1 (sv) |
| GB (1) | GB1153205A (sv) |
| NL (1) | NL132731C (sv) |
| NO (2) | NO124646B (sv) |
| SE (1) | SE332715B (sv) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3497572A (en) * | 1967-08-24 | 1970-02-24 | Phillips Petroleum Co | High impact resin compositions |
| US3499949A (en) * | 1967-09-29 | 1970-03-10 | Phillips Petroleum Co | Reaction of peroxides with blends of polystyrene,resinous block copolymer,and rubbery polymer of an oxirane |
| JPS4925044A (sv) * | 1969-02-27 | 1974-03-06 | ||
| US3695477A (en) * | 1970-05-18 | 1972-10-03 | Grace W R & Co | Plastisols and gaskets |
| US3800007A (en) * | 1971-10-18 | 1974-03-26 | Pennwalt Corp | Process for preparing block copolymers with peroxy containing chain- transfer agents and products |
| US3907931A (en) * | 1972-01-05 | 1975-09-23 | Gen Tire & Rubber Co | High impact two-component polystyrene blends |
| US3907929A (en) * | 1972-01-05 | 1975-09-23 | Gen Tire & Rubber Co | Compatible three-component polymer alloys |
| US3906058A (en) * | 1972-02-24 | 1975-09-16 | Gen Tire & Rubber Co | High impact two-component resin blends |
| US3907930A (en) * | 1973-11-09 | 1975-09-23 | Monsanto Co | Toughened polymeric polyblend having high flow and ductility |
| US3936365A (en) * | 1974-05-28 | 1976-02-03 | The Dow Chemical Company | Radiation crosslinked block copolymer blends with improved impact resistance |
| US4267284A (en) * | 1977-01-07 | 1981-05-12 | Phillips Petroleum Company | Tough, transparent articles from styrene polymers blended with certain block-random copolymers |
| US4239859A (en) * | 1979-08-29 | 1980-12-16 | Shell Oil Company | High impact polystyrene blend compositions |
| US4739525A (en) * | 1985-06-11 | 1988-04-26 | American Standard, Inc. | Self-contained toilet system |
| US5252664A (en) * | 1989-07-21 | 1993-10-12 | Polysar Limited | Transparent toughened thermoplastics |
| US5079296A (en) * | 1989-07-21 | 1992-01-07 | Polysar Limited | Transparent toughened thermoplastics |
| US5385963A (en) * | 1992-01-30 | 1995-01-31 | Gencorp Inc. | Unsaturated polyester-modified flexible copolymers for use in sheet molding compositions |
| US5362819A (en) * | 1992-01-30 | 1994-11-08 | Gencorp Inc. | Polyester-flexible polymer block copolymers and mixtures thereof |
| US5334441A (en) * | 1992-01-30 | 1994-08-02 | Gencorp Inc. | Composite comprising unsaturated polyester-flexible polymer block copolymer coated fiber structures in a polyester or vinyl ester resin matrix |
| US5428068A (en) * | 1992-01-30 | 1995-06-27 | Gencorp Inc. | Unsaturated polyester-modified flexible polymers for use in molding composition |
| US5342554A (en) * | 1993-01-07 | 1994-08-30 | Gencorp Inc. | Vinyl-terminated polyesters and polycarbonates for flexibilizing and improving the toughness of compositions from unsaturated polyesters and fiber reinforced plastics made from them |
| US5376721A (en) * | 1993-01-29 | 1994-12-27 | Gencorp Inc. | Low-profile additives for thermosetting polyester compositions |
| DE4445141A1 (de) * | 1994-12-17 | 1996-06-20 | Basf Ag | Verfahren zur Herstellung von schlagzäh modifizierten Polystyrol-Formmassen |
| US9193839B2 (en) * | 2014-03-14 | 2015-11-24 | Fina Technology, Inc. | Crosslinking control in high impact polystyrene manufacturing process |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1069818B (de) * | 1958-10-29 | 1959-11-26 | The Dow Chemical Company, Midland, Mich. (V. St. A.) | Verfahren zur Herstellung von verformbaren Lösungen aus Polyacrylnitril |
| US2844562A (en) * | 1955-05-16 | 1958-07-22 | Alvin R Ingram | Method of mixing resinous polymeric styrene with a rubbery butadiene polymer |
| BE613240A (sv) * | 1961-01-30 | |||
| US3264374A (en) * | 1963-01-02 | 1966-08-02 | Monsanto Co | Graft copolymer formed by polymerizing butadiene in styrene with an alkylli catalyst, deactivating the catalyst and adding an organic peroxide |
| US3264375A (en) * | 1963-01-16 | 1966-08-02 | Monsanto Co | Process for the graft polymerization of styrene on alkyl lithium catalyzed polybutadiene using a peroxide catalyst |
| US3251905A (en) * | 1963-08-05 | 1966-05-17 | Phillips Petroleum Co | Method of preparing block copolymers of conjugated dienes and vinyl-substituted aromatic compounds using dilithio catalysts and diluent mixture of hydrocarbon and ether |
| US3231635A (en) * | 1963-10-07 | 1966-01-25 | Shell Oil Co | Process for the preparation of block copolymers |
-
1965
- 1965-09-07 US US485625A patent/US3429951A/en not_active Expired - Lifetime
-
1966
- 1966-01-05 US US518783A patent/US3476829A/en not_active Expired - Lifetime
- 1966-08-29 ES ES0330671A patent/ES330671A1/es not_active Expired
- 1966-09-06 SE SE11964/66A patent/SE332715B/xx unknown
- 1966-09-06 NL NL6612517A patent/NL132731C/xx active
- 1966-09-06 DE DE1694749A patent/DE1694749B2/de active Granted
- 1966-09-06 DK DK458566AA patent/DK112898B/da unknown
- 1966-09-06 GB GB39771/66A patent/GB1153205A/en not_active Expired
- 1966-09-07 BE BE686558D patent/BE686558A/xx unknown
- 1966-09-07 NO NO164596A patent/NO124646B/no unknown
-
1971
- 1971-01-04 NO NO00011/71A patent/NO127619B/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE1694749B2 (de) | 1975-02-06 |
| DK112898B (da) | 1969-01-27 |
| SE332715B (sv) | 1971-02-15 |
| GB1153205A (en) | 1969-05-29 |
| ES330671A1 (es) | 1967-06-16 |
| NL132731C (sv) | 1971-06-15 |
| DE1694749A1 (de) | 1970-12-17 |
| US3429951A (en) | 1969-02-25 |
| NL6612517A (sv) | 1967-03-08 |
| US3476829A (en) | 1969-11-04 |
| NO127619B (sv) | 1973-07-23 |
| BE686558A (sv) | 1967-03-07 |
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