NO119471B - - Google Patents

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Info

Publication number: NO119471B
Authority: NO; Norway
Prior art keywords: retrocortin; compound; chloroform; acetoxy; solution
Prior art date: 1963-10-02

Application number

NO153354A

Other languages

English (en)

Norwegian (no)

Inventor

J Soila

E Niskanen

Original Assignee

Koltek Oy

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1963-10-02

Filing date

1964-05-23

Publication date

1970-05-19

1964-05-23 Application filed by Koltek Oy filed Critical Koltek Oy

1970-05-19 Publication of NO119471B publication Critical patent/NO119471B/no

Links

150000001875 compounds Chemical class 0.000 claims description 19
239000007858 starting material Substances 0.000 claims description 9
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 claims description 7
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 claims description 7
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 claims description 7
229960004544 cortisone Drugs 0.000 claims description 7
229910052739 hydrogen Inorganic materials 0.000 claims description 7
239000001257 hydrogen Substances 0.000 claims description 7
238000000034 method Methods 0.000 claims description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
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 claims description 3
239000003638 chemical reducing agent Substances 0.000 claims description 3
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 3
239000011734 sodium Substances 0.000 claims description 3
229910052708 sodium Inorganic materials 0.000 claims description 3
229930194542 Keto Natural products 0.000 claims description 2
206010041277 Sodium retention Diseases 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
150000002367 halogens Chemical class 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
125000000468 ketone group Chemical group 0.000 claims description 2
238000002360 preparation method Methods 0.000 claims description 2
150000003461 sulfonyl halides Chemical class 0.000 claims description 2
229940126214 compound 3 Drugs 0.000 claims 1
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 36
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 28
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
239000000243 solution Substances 0.000 description 21
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
239000000203 mixture Substances 0.000 description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
229960005205 prednisolone Drugs 0.000 description 15
229960000583 acetic acid Drugs 0.000 description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
238000006243 chemical reaction Methods 0.000 description 9
239000012362 glacial acetic acid Substances 0.000 description 8
239000002026 chloroform extract Substances 0.000 description 7
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 6
229910052794 bromium Inorganic materials 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
OIGNJSKKLXVSLS-VWUMJDOOSA-N prednisolone Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OIGNJSKKLXVSLS-VWUMJDOOSA-N 0.000 description 5
238000010992 reflux Methods 0.000 description 5
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 description 4
UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 description 4
230000000694 effects Effects 0.000 description 4
GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
238000007865 diluting Methods 0.000 description 3
239000005457 ice water Substances 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
239000002904 solvent Substances 0.000 description 3
239000000126 substance Substances 0.000 description 3
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 3
239000000725 suspension Substances 0.000 description 3
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
229910021555 Chromium Chloride Inorganic materials 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
239000012359 Methanesulfonyl chloride Substances 0.000 description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
BMGBMKTZPIZHMZ-CSDMTUIFSA-N [2-[(8S,9S,10S,13S,14S,17R)-2-bromo-17-hydroxy-10,13-dimethyl-3,11-dioxo-1,2,4,5,6,7,8,9,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-yl]-2-oxoethyl] acetate Chemical compound O=C1CC2CC[C@@H]3[C@H](C(C[C@@]4([C@](CC[C@H]43)(C(COC(C)=O)=O)O)C)=O)[C@]2(CC1Br)C BMGBMKTZPIZHMZ-CSDMTUIFSA-N 0.000 description 2
QSWDMMVNRMROPK-UHFFFAOYSA-K chromium(3+) trichloride Chemical compound [Cl-].[Cl-].[Cl-].[Cr+3] QSWDMMVNRMROPK-UHFFFAOYSA-K 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
239000012452 mother liquor Substances 0.000 description 2
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
238000003756 stirring Methods 0.000 description 2
CXBDYQVECUFKRK-UHFFFAOYSA-N 1-methoxybutane Chemical compound CCCCOC CXBDYQVECUFKRK-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
206010030113 Oedema Diseases 0.000 description 1
SUYDMLDXAOBPDP-ZJRBNCAOSA-N [2-[(8S,9S,10R,13S,14S,17R)-4-bromo-17-hydroxy-10,13-dimethyl-3,11-dioxo-1,2,4,5,6,7,8,9,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-yl]-2-oxoethyl] acetate Chemical compound BrC1C2CC[C@H]3[C@@H]4CC[C@](C(COC(C)=O)=O)([C@]4(CC([C@@H]3[C@]2(CCC1=O)C)=O)C)O SUYDMLDXAOBPDP-ZJRBNCAOSA-N 0.000 description 1
AZCNJEFLSOQGST-BPSNTZLWSA-N [2-[(8s,9s,10s,13s,14s,17r)-17-hydroxy-10,13-dimethyl-3,11-dioxo-1,2,4,5,6,7,8,9,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-yl]-2-oxoethyl] acetate Chemical compound C1CC2CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)COC(=O)C)(O)[C@@]1(C)CC2=O AZCNJEFLSOQGST-BPSNTZLWSA-N 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
206010003246 arthritis Diseases 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
FRYHCSODNHYDPU-UHFFFAOYSA-N ethanesulfonyl chloride Chemical compound CCS(Cl)(=O)=O FRYHCSODNHYDPU-UHFFFAOYSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
230000036571 hydration Effects 0.000 description 1
238000006703 hydration reaction Methods 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
239000012535 impurity Substances 0.000 description 1
230000001939 inductive effect Effects 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
230000004060 metabolic process Effects 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
HBEQXAKJSGXAIQ-UHFFFAOYSA-N oxopalladium Chemical compound [Pd]=O HBEQXAKJSGXAIQ-UHFFFAOYSA-N 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
229910003445 palladium oxide Inorganic materials 0.000 description 1
230000007331 pathological accumulation Effects 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
239000000047 product Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
235000009518 sodium iodide Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
150000003431 steroids Chemical class 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1

Classifications

- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F16—ENGINEERING ELEMENTS AND UNITS; GENERAL MEASURES FOR PRODUCING AND MAINTAINING EFFECTIVE FUNCTIONING OF MACHINES OR INSTALLATIONS; THERMAL INSULATION IN GENERAL
- F16G—BELTS, CABLES, OR ROPES, PREDOMINANTLY USED FOR DRIVING PURPOSES; CHAINS; FITTINGS PREDOMINANTLY USED THEREFOR
- F16G13/00—Chains
- F16G13/12—Hauling- or hoisting-chains so called ornamental chains
- B—PERFORMING OPERATIONS; TRANSPORTING
- B65—CONVEYING; PACKING; STORING; HANDLING THIN OR FILAMENTARY MATERIAL
- B65G—TRANSPORT OR STORAGE DEVICES, e.g. CONVEYORS FOR LOADING OR TIPPING, SHOP CONVEYOR SYSTEMS OR PNEUMATIC TUBE CONVEYORS
- B65G17/00—Conveyors having an endless traction element, e.g. a chain, transmitting movement to a continuous or substantially-continuous load-carrying surface or to a series of individual load-carriers; Endless-chain conveyors in which the chains form the load-carrying surface
- B65G17/30—Details; Auxiliary devices
- B65G17/38—Chains or like traction elements; Connections between traction elements and load-carriers
- B—PERFORMING OPERATIONS; TRANSPORTING
- B65—CONVEYING; PACKING; STORING; HANDLING THIN OR FILAMENTARY MATERIAL
- B65G—TRANSPORT OR STORAGE DEVICES, e.g. CONVEYORS FOR LOADING OR TIPPING, SHOP CONVEYOR SYSTEMS OR PNEUMATIC TUBE CONVEYORS
- B65G2201/00—Indexing codes relating to handling devices, e.g. conveyors, characterised by the type of product or load being conveyed or handled
- B65G2201/06—Articles and bulk

Landscapes

Engineering & Computer Science (AREA)
General Engineering & Computer Science (AREA)
Mechanical Engineering (AREA)
Chain Conveyers (AREA)
Steroid Compounds (AREA)

NO153354A 1963-10-02 1964-05-23 NO119471B (sv)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DEK0050979		1963-10-02

Publications (1)

Publication Number	Publication Date
NO119471B true NO119471B (sv)	1970-05-19

Family

ID=7225830

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO153354A NO119471B (sv)	1963-10-02	1964-05-23

Country Status (4)

Country	Link
US (1)	US3268063A (sv)
DK (1)	DK113681B (sv)
GB (1)	GB1060261A (sv)
NO (1)	NO119471B (sv)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
USRE28746E (en) *	1970-10-20	1976-03-30	Bruce P	Chain cable
DE3404268A1 (de) *	1984-02-03	1985-08-14	Rud-Kettenfabrik Rieger & Dietz Gmbh U. Co, 7080 Aalen	Anordnung zum verbinden eines ovalen kettengliedes mit einem bolzen
TWI280186B (en) *	2004-03-03	2007-05-01	Chum Power Machinery Corp	Method for easily adjusting distance between pre-forms and structure thereof

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2066723A (en) *	1934-06-11	1937-01-05	Standard Conveyor Co	Conveyer chain
US2960210A (en) *	1957-06-19	1960-11-15	Charles T Jorgensen	Conveyor chain

1964
- 1964-05-23 NO NO153354A patent/NO119471B/no unknown
- 1964-05-26 US US370169A patent/US3268063A/en not_active Expired - Lifetime
- 1964-05-30 DK DK271764AA patent/DK113681B/da unknown
- 1964-06-09 GB GB23898/64A patent/GB1060261A/en not_active Expired

Also Published As

Publication number	Publication date
US3268063A (en)	1966-08-23
GB1060261A (en)	1967-03-01
DK113681B (da)	1969-04-14

Publication	Publication Date	Title
US2912446A (en)	1959-11-10	delta1, 4-3, 20-diketo-11-oxygenated-17alpha-hydroxy-pregnadienes and 9-fluoro derivatives thereof
US2782211A (en)	1957-02-19	Manufacture of dehydro compounds of the pregnane series
US2541104A (en)	1951-02-13	17(alpha)-hydroxy-20-ketosteroids and process
NO119467B (sv)	1970-05-19
NO132558B (sv)	1975-08-18
NO143159B (no)	1980-09-15	Fremgangsmaate for fremstilling av metylmetakrylat-alkylakrylatkopolymerer.
US2879279A (en)	1959-03-24	Preparation of unsaturated compounds of the cyclopentanopolyhydrophenanthrene series
DE1468035A1 (de)	1968-12-12	Verfahren zur Herstellung von 19-Alkylsteroiden
NO119471B (sv)	1970-05-19
US4325879A (en)	1982-04-20	Amino-14 steroid derivatives and process for preparation of the same
US2275790A (en)	1942-03-10	Aldehydes of the saturated and unsaturated pregnane-series and process of making same
US2408834A (en)	1946-10-08	Steroidal compounds and methods for obtaining the same
NO128976B (sv)	1974-02-04
US2732383A (en)	1956-01-24	Pregnadeenes and method of preparing
FRIED et al.	1942	STUDIES ON LACTONES RELATED TO THE CARDIAC AGLYCONES. VII. SYNTHESIS OF 3, 14-BISDESOXYTHEVETIGENIN AND OF 14-DESOXYTHEVETIGENIN
NO119468B (sv)	1970-05-19
US2912432A (en)	1959-11-10	3-oxo and 3-hydroxy derivatives of 18-dimethyl-aminopregn-20-enes and intermediates
US2846456A (en)	1958-08-05	Steroid 21-aldehydes
CH494213A (de)	1970-07-31	Verfahren zur Herstellung von Gonadienonen
NO121103B (sv)	1971-01-18
US3189597A (en)	1965-06-15	3-glycosides of 17-amino-3-hydroxy-5-androstenes
US2749356A (en)	1956-06-05	Method of isolating and purifying keto steroids and new keto steroid compounds
NO119754B (sv)	1970-06-29
US3083198A (en)	1963-03-26	Novel 2-alkoxy steroids and processes for preparing the same
US3087941A (en)	1963-04-30	17alpha-bromo-6-methyl-pregnane derivatives