NO132939B - - Google Patents
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- NO132939B NO132939B NO1651/72A NO165172A NO132939B NO 132939 B NO132939 B NO 132939B NO 1651/72 A NO1651/72 A NO 1651/72A NO 165172 A NO165172 A NO 165172A NO 132939 B NO132939 B NO 132939B
- Authority
- NO
- Norway
- Prior art keywords
- compounds
- chloro
- ones
- androstene
- androstan
- Prior art date
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- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 11
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- 230000001548 androgenic effect Effects 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 6
- 230000000694 effects Effects 0.000 claims description 6
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 6
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 6
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 4
- 150000003431 steroids Chemical class 0.000 claims description 4
- 238000006136 alcoholysis reaction Methods 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- 150000007530 organic bases Chemical group 0.000 claims description 2
- MBEVSMZJMIQVBG-UHFFFAOYSA-N 2-(hydroxymethyl)guanidine Chemical compound NC(N)=NCO MBEVSMZJMIQVBG-UHFFFAOYSA-N 0.000 abstract 1
- 238000009413 insulation Methods 0.000 abstract 1
- 210000002268 wool Anatomy 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- 239000000243 solution Substances 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 8
- 239000000155 melt Substances 0.000 description 7
- 230000001195 anabolic effect Effects 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 235000019260 propionic acid Nutrition 0.000 description 4
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testostosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- ZXUDUPMTNHRALN-UHFFFAOYSA-N 2-cyclopentylpropanoyl 2-cyclopentylpropanoate Chemical compound C1CCCC1C(C)C(=O)OC(=O)C(C)C1CCCC1 ZXUDUPMTNHRALN-UHFFFAOYSA-N 0.000 description 1
- GCKMFJBGXUYNAG-HLXURNFRSA-N Methyltestosterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@](C)(O)[C@@]1(C)CC2 GCKMFJBGXUYNAG-HLXURNFRSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- XENVCRGQTABGKY-ZHACJKMWSA-N chlorohydrin Chemical compound CC#CC#CC#CC#C\C=C\C(Cl)CO XENVCRGQTABGKY-ZHACJKMWSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 229960001566 methyltestosterone Drugs 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229960003604 testosterone Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B19/00—Layered products comprising a layer of natural mineral fibres or particles, e.g. asbestos, mica
- B32B19/04—Layered products comprising a layer of natural mineral fibres or particles, e.g. asbestos, mica next to another layer of the same or of a different material
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B5/00—Layered products characterised by the non- homogeneity or physical structure, i.e. comprising a fibrous, filamentary, particulate or foam layer; Layered products characterised by having a layer differing constitutionally or physically in different parts
- B32B5/02—Layered products characterised by the non- homogeneity or physical structure, i.e. comprising a fibrous, filamentary, particulate or foam layer; Layered products characterised by having a layer differing constitutionally or physically in different parts characterised by structural features of a fibrous or filamentary layer
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B7/00—Layered products characterised by the relation between layers; Layered products characterised by the relative orientation of features between layers, or by the relative values of a measurable parameter between layers, i.e. products comprising layers having different physical, chemical or physicochemical properties; Layered products characterised by the interconnection of layers
- B32B7/04—Interconnection of layers
- B32B7/12—Interconnection of layers using interposed adhesives or interposed materials with bonding properties
-
- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B30/00—Compositions for artificial stone, not containing binders
- C04B30/02—Compositions for artificial stone, not containing binders containing fibrous materials
-
- D—TEXTILES; PAPER
- D04—BRAIDING; LACE-MAKING; KNITTING; TRIMMINGS; NON-WOVEN FABRICS
- D04H—MAKING TEXTILE FABRICS, e.g. FROM FIBRES OR FILAMENTARY MATERIAL; FABRICS MADE BY SUCH PROCESSES OR APPARATUS, e.g. FELTS, NON-WOVEN FABRICS; COTTON-WOOL; WADDING ; NON-WOVEN FABRICS FROM STAPLE FIBRES, FILAMENTS OR YARNS, BONDED WITH AT LEAST ONE WEB-LIKE MATERIAL DURING THEIR CONSOLIDATION
- D04H1/00—Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres
- D04H1/40—Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres from fleeces or layers composed of fibres without existing or potential cohesive properties
- D04H1/42—Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres from fleeces or layers composed of fibres without existing or potential cohesive properties characterised by the use of certain kinds of fibres insofar as this use has no preponderant influence on the consolidation of the fleece
- D04H1/4209—Inorganic fibres
-
- D—TEXTILES; PAPER
- D04—BRAIDING; LACE-MAKING; KNITTING; TRIMMINGS; NON-WOVEN FABRICS
- D04H—MAKING TEXTILE FABRICS, e.g. FROM FIBRES OR FILAMENTARY MATERIAL; FABRICS MADE BY SUCH PROCESSES OR APPARATUS, e.g. FELTS, NON-WOVEN FABRICS; COTTON-WOOL; WADDING ; NON-WOVEN FABRICS FROM STAPLE FIBRES, FILAMENTS OR YARNS, BONDED WITH AT LEAST ONE WEB-LIKE MATERIAL DURING THEIR CONSOLIDATION
- D04H1/00—Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres
- D04H1/40—Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres from fleeces or layers composed of fibres without existing or potential cohesive properties
- D04H1/42—Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres from fleeces or layers composed of fibres without existing or potential cohesive properties characterised by the use of certain kinds of fibres insofar as this use has no preponderant influence on the consolidation of the fleece
- D04H1/4209—Inorganic fibres
- D04H1/4218—Glass fibres
-
- D—TEXTILES; PAPER
- D04—BRAIDING; LACE-MAKING; KNITTING; TRIMMINGS; NON-WOVEN FABRICS
- D04H—MAKING TEXTILE FABRICS, e.g. FROM FIBRES OR FILAMENTARY MATERIAL; FABRICS MADE BY SUCH PROCESSES OR APPARATUS, e.g. FELTS, NON-WOVEN FABRICS; COTTON-WOOL; WADDING ; NON-WOVEN FABRICS FROM STAPLE FIBRES, FILAMENTS OR YARNS, BONDED WITH AT LEAST ONE WEB-LIKE MATERIAL DURING THEIR CONSOLIDATION
- D04H1/00—Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres
- D04H1/40—Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres from fleeces or layers composed of fibres without existing or potential cohesive properties
- D04H1/58—Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres from fleeces or layers composed of fibres without existing or potential cohesive properties by applying, incorporating or activating chemical or thermoplastic bonding agents, e.g. adhesives
- D04H1/593—Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres from fleeces or layers composed of fibres without existing or potential cohesive properties by applying, incorporating or activating chemical or thermoplastic bonding agents, e.g. adhesives to layered webs
-
- D—TEXTILES; PAPER
- D04—BRAIDING; LACE-MAKING; KNITTING; TRIMMINGS; NON-WOVEN FABRICS
- D04H—MAKING TEXTILE FABRICS, e.g. FROM FIBRES OR FILAMENTARY MATERIAL; FABRICS MADE BY SUCH PROCESSES OR APPARATUS, e.g. FELTS, NON-WOVEN FABRICS; COTTON-WOOL; WADDING ; NON-WOVEN FABRICS FROM STAPLE FIBRES, FILAMENTS OR YARNS, BONDED WITH AT LEAST ONE WEB-LIKE MATERIAL DURING THEIR CONSOLIDATION
- D04H1/00—Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres
- D04H1/40—Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres from fleeces or layers composed of fibres without existing or potential cohesive properties
- D04H1/58—Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres from fleeces or layers composed of fibres without existing or potential cohesive properties by applying, incorporating or activating chemical or thermoplastic bonding agents, e.g. adhesives
- D04H1/64—Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres from fleeces or layers composed of fibres without existing or potential cohesive properties by applying, incorporating or activating chemical or thermoplastic bonding agents, e.g. adhesives the bonding agent being applied in wet state, e.g. chemical agents in dispersions or solutions
-
- D—TEXTILES; PAPER
- D04—BRAIDING; LACE-MAKING; KNITTING; TRIMMINGS; NON-WOVEN FABRICS
- D04H—MAKING TEXTILE FABRICS, e.g. FROM FIBRES OR FILAMENTARY MATERIAL; FABRICS MADE BY SUCH PROCESSES OR APPARATUS, e.g. FELTS, NON-WOVEN FABRICS; COTTON-WOOL; WADDING ; NON-WOVEN FABRICS FROM STAPLE FIBRES, FILAMENTS OR YARNS, BONDED WITH AT LEAST ONE WEB-LIKE MATERIAL DURING THEIR CONSOLIDATION
- D04H1/00—Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres
- D04H1/70—Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres characterised by the method of forming fleeces or layers, e.g. reorientation of fibres
- D04H1/74—Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres characterised by the method of forming fleeces or layers, e.g. reorientation of fibres the fibres being orientated, e.g. in parallel (anisotropic fleeces)
-
- E—FIXED CONSTRUCTIONS
- E04—BUILDING
- E04B—GENERAL BUILDING CONSTRUCTIONS; WALLS, e.g. PARTITIONS; ROOFS; FLOORS; CEILINGS; INSULATION OR OTHER PROTECTION OF BUILDINGS
- E04B1/00—Constructions in general; Structures which are not restricted either to walls, e.g. partitions, or floors or ceilings or roofs
- E04B1/62—Insulation or other protection; Elements or use of specified material therefor
- E04B1/74—Heat, sound or noise insulation, absorption, or reflection; Other building methods affording favourable thermal or acoustical conditions, e.g. accumulating of heat within walls
- E04B1/76—Heat, sound or noise insulation, absorption, or reflection; Other building methods affording favourable thermal or acoustical conditions, e.g. accumulating of heat within walls specifically with respect to heat only
- E04B1/7654—Heat, sound or noise insulation, absorption, or reflection; Other building methods affording favourable thermal or acoustical conditions, e.g. accumulating of heat within walls specifically with respect to heat only comprising an insulating layer, disposed between two longitudinal supporting elements, e.g. to insulate ceilings
- E04B1/7658—Heat, sound or noise insulation, absorption, or reflection; Other building methods affording favourable thermal or acoustical conditions, e.g. accumulating of heat within walls specifically with respect to heat only comprising an insulating layer, disposed between two longitudinal supporting elements, e.g. to insulate ceilings comprising fiber insulation, e.g. as panels or loose filled fibres
- E04B1/7662—Heat, sound or noise insulation, absorption, or reflection; Other building methods affording favourable thermal or acoustical conditions, e.g. accumulating of heat within walls specifically with respect to heat only comprising an insulating layer, disposed between two longitudinal supporting elements, e.g. to insulate ceilings comprising fiber insulation, e.g. as panels or loose filled fibres comprising fiber blankets or batts
-
- E—FIXED CONSTRUCTIONS
- E04—BUILDING
- E04B—GENERAL BUILDING CONSTRUCTIONS; WALLS, e.g. PARTITIONS; ROOFS; FLOORS; CEILINGS; INSULATION OR OTHER PROTECTION OF BUILDINGS
- E04B1/00—Constructions in general; Structures which are not restricted either to walls, e.g. partitions, or floors or ceilings or roofs
- E04B1/62—Insulation or other protection; Elements or use of specified material therefor
- E04B1/74—Heat, sound or noise insulation, absorption, or reflection; Other building methods affording favourable thermal or acoustical conditions, e.g. accumulating of heat within walls
- E04B1/76—Heat, sound or noise insulation, absorption, or reflection; Other building methods affording favourable thermal or acoustical conditions, e.g. accumulating of heat within walls specifically with respect to heat only
- E04B1/78—Heat insulating elements
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B2307/00—Properties of the layers or laminate
- B32B2307/30—Properties of the layers or laminate having particular thermal properties
- B32B2307/304—Insulating
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B2315/00—Other materials containing non-metallic inorganic compounds not provided for in groups B32B2311/00 - B32B2313/04
- B32B2315/14—Mineral wool
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B2471/00—Floor coverings
- B32B2471/04—Mats
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A30/00—Adapting or protecting infrastructure or their operation
- Y02A30/24—Structural elements or technologies for improving thermal insulation
- Y02A30/244—Structural elements or technologies for improving thermal insulation using natural or recycled building materials, e.g. straw, wool, clay or used tires
Landscapes
- Engineering & Computer Science (AREA)
- Chemical & Material Sciences (AREA)
- Textile Engineering (AREA)
- Physics & Mathematics (AREA)
- Architecture (AREA)
- Structural Engineering (AREA)
- Inorganic Chemistry (AREA)
- Ceramic Engineering (AREA)
- Civil Engineering (AREA)
- Electromagnetism (AREA)
- Acoustics & Sound (AREA)
- Materials Engineering (AREA)
- General Chemical & Material Sciences (AREA)
- Dispersion Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Laminated Bodies (AREA)
- Paper (AREA)
- Thermal Insulation (AREA)
- Building Environments (AREA)
- Nonwoven Fabrics (AREA)
Abstract
ineralullmatte for varme- og kuldeisolasjon.ineral wool mat for heat and cold insulation.
Description
Fremgangsmåte til fremstilling av 2-klor- A 1-androsten-17,^-ol-3-oner og 17-estere av sådanne forbindelser. Process for the preparation of 2-chloro-A 1-androsten-17,^-ol-3-ones and 17-esters of such compounds.
Fremstilling av preparater som sam-men med en sterk anabolisk aktivitet viser Production of preparations which together with a strong anabolic activity show
minst mulig androgene bivirkninger er av the least possible androgenic side effects are off
stor betydning for terapeutiske formål. Det great importance for therapeutic purposes. The
er kjent noen steroider som står nær te-stosteronet og som i sammenligning med are known some steroids that stand close to the te-stosterone and which in comparison with
testosteron viser en litt øket anabolisk testosterone shows a slightly increased anabolic
virkning og samtidig en merkbart minsket effect and at the same time a noticeably reduced
androgen virkning. Minskningen i den androgenic effect. The decrease in it
androgene virkning er imidlertid ikke så however, androgenic action is not so
utpreget hos disse steroider at den ikke distinctly with these steroids that it does not
griper forstyrrende inn ved doser som er intervenes disturbingly at doses that are
nødvendige til å oppnå en tilstrekkelig anabolisk virkning. Å finne nye forbindelser necessary to achieve a sufficient anabolic effect. Finding new connections
med en ytterligere forskyvning av forholdet with a further shift in the ratio
i deres aktivitet til gunst for den anaboliske in their activity in favor of the anabolic
virkning, ville derfor bety et ubestridelig effect, would therefore mean an undeniable
fremskritt. progress.
Det ble nu funnet det overraskende It was now found that surprisingly
forhold at innføring av et kloratom i 2-stillingen i de anabolisk virkende A<*->androsten-17-ol-3-oner og 17-estere av disse, the fact that introduction of a chlorine atom in the 2-position in the anabolic-acting A<*->androsten-17-ol-3-ones and 17-esters thereof,
forårsaker en slik forskyvning i aktivitets-forholdet. Således viser f. eks. 2-klor-A<1->causes such a shift in the activity ratio. Thus, e.g. 2-chloro-A<1->
androsten 17(3-ol-3-on i sammenligning androsten 17(3-ol-3-one in comparison
med den klorfri forbindelse en minskning with the chlorine-free compound a reduction
av den androgene virkning på omkring en of the androgenic effect on about one
femtedel, under bibeholdelse av den samme fifth, retaining the same
anaboliske virkning. anabolic effect.
Ved hjelp av oppfinnelsen skaffes der følgelig en fremgangsmåte til fremstilling av 2-klor-A<1->androsten-17-(3-ol-3-on-forbindelser som eventuelt er forestret i 17(3-stillingen, eller 1- og 17«-metyl-homologe eller 19-nor-homologe av disse forbindelser som er anabolisk aktive steroider med liten androgen bevirkning. Det karakteris-tiske hovedtrekk ved fremgangsmåten be-står i at l,2-oxido-androstan-17|3-ol-3-oner, eller det alkoholyseprodukt som fåes ved behandling av disse forbindelser med metanol i nærvær av perklorsyre, behandles med hydrogenklorid i kloroform, eller 2 atomer klor adderes til A^androsten-17(3-ol-3-oner, og 1 mol hydrogenklorid deretter avspaltes fra de herved erholdte l,2-diklor-androstan-17|3-ol-3-oner ved behandling med en tertiær organisk base, fortrinsvis pyridin, hvorpå 17(3-hydroxyl-gruppen i de således erholdte forbindelser eventuelt acyleres med fysiologisk tålbare syrer. With the help of the invention, a method for the production of 2-chloro-A<1->androstene-17-(3-ol-3-one compounds which are optionally esterified in the 17(3-position, or 1- and 17"-methyl-homologous or 19-nor-homologous of these compounds which are anabolically active steroids with little androgenic effect. The characteristic main feature of the method is that 1,2-oxido-androstan-17|3-ol -3-ones, or the alcoholysis product obtained by treating these compounds with methanol in the presence of perchloric acid, is treated with hydrogen chloride in chloroform, or 2 atoms of chlorine are added to A^androstene-17(3-ol-3-ones, and 1 moles of hydrogen chloride are then split off from the 1,2-dichloro-androstan-17|3-ol-3-ones thus obtained by treatment with a tertiary organic base, preferably pyridine, whereupon the 17(3-hydroxyl group in the thus obtained compounds optionally acylated with physiologically tolerable acids.
Behandler man f. eks. 1,2-oxido-an-drostan-17(3-ol-3-on med hydrogenklorid i kloroform så dannes i stedet for det klor-hydrin man skulle vente å få, umiddelbart dettes vannavspaltningsprodukt, nemlig 2-klor-A,-androsten-17(3-ol-3-on: If you treat e.g. 1,2-oxido-androstan-17(3-ol-3-one with hydrogen chloride in chloroform then instead of the chlorohydrin one would expect to get, its water splitting product is immediately formed, namely 2-chloro-A,- androsten-17(3-ol-3-one:
Behandles eksempelvis ""netanolyse-produktet av 1,2-oxido-andrc ,an-17-ol-3-on — hvilket kan fåes av dette som oven-for beskrevet — med hydrogenklorid i kloroform, så dannes ganske uventet 2-klor-/V-androsten-lVp-ol-S-on: If, for example, the netanolysis product of 1,2-oxido-andrc,an-17-ol-3-one — which can be obtained from this as described above — is treated with hydrogen chloride in chloroform, quite unexpectedly 2-chloro- /V-androstene-lVp-ol-S-one:
I det følgende beskrives som eksemp-ler noen utførelsesformer for oppfinnelsen. In the following, some embodiments of the invention are described as examples.
Eksempel 1. Example 1.
200 mg l,2-oxido-androstan-17(3-ol-3-on oppløses i 25 ml alkoholfri kloroform. Tørr saltsyregass ledes ved 0° C i 2 timer inn i den erholdte oppløsning. Der fortynnes derpå med vann og ekstraheres med methylenklorid. Metylenkloridekstraktet vaskes med vann til det er nøytralt og tørres derpå over natriumsulfat. Oppløs-ningsmidlet fordampes og residuet rives med eter, hvorpå væsken suges bort fra det faste stoff. Dette omkrystalliseres fra eddikester, hvorved man får 2-klor-A<1->androsten-17(3-ol-3-on som smelter ved 221—222° C. UV:E,,S = 9500. Dissolve 200 mg of 1,2-oxido-androstan-17(3-ol-3-one in 25 ml of alcohol-free chloroform. Dry hydrochloric acid gas is introduced at 0° C for 2 hours into the resulting solution. It is then diluted with water and extracted with methylene chloride. The methylene chloride extract is washed with water until it is neutral and then dried over sodium sulfate. The solvent is evaporated and the residue is triturated with ether, after which the liquid is sucked away from the solid. This is recrystallized from acetic acid, whereby 2-chloro-A<1 ->androsten-17(3-ol-3-one which melts at 221-222° C. UV:E,,S = 9500.
Eksempel 2. Example 2.
Alkoholyseproduktet av 1,2-oxido-an-drostan som anvendes som utgangsmate-riale fåes ved at man behandler 3,2 g 1,2a-oxido-androstan-17(3-ol-3-on i 200 ml metanol med 1,3 ml 70 pst.'s perklorsyre stå i 16 timer ved romtemperatur. Det herved erholdte stoff opparbeides som angitt i eksempel 1. Det erholdte residuum rives med metanol, hvorpå væsken suges bort og det faste stoff tørres. Det tørre råprodukt (med 9,4 pst. OCK, og som er inaktivt i spektrets ultrafiolette område) smelter ved 77—81° C. Det behandles således som beskrevet i eksempel 1 med saltsyregass i kloroform, opparbeides og omkrystalliseres. Utbytte 2,9 g. Etter omkrystallisasjon smelter 2-klor-A<1->androsten-17p-ol-3-on ved 221—222° C. UV:e2JS = 9500. I blanding med den forbindelse som fåes ved å gå frem som angitt i eksempel 1 nedsettes nevnte forbindelses smeltepunkt ikke. The alcoholysis product of 1,2-oxido-androstane, which is used as starting material, is obtained by treating 3.2 g of 1,2a-oxido-androstan-17(3-ol-3-one in 200 ml of methanol with 1, 3 ml of 70% perchloric acid stand for 16 hours at room temperature. The material obtained is worked up as indicated in example 1. The residue obtained is triturated with methanol, after which the liquid is sucked off and the solid is dried. The dry crude product (with 9, 4 percent OCK, and which is inactive in the ultraviolet region of the spectrum) melts at 77-81° C. It is thus treated as described in example 1 with hydrochloric acid gas in chloroform, worked up and recrystallized. Yield 2.9 g. After recrystallization, 2- chloro-A<1->androsten-17p-ol-3-one at 221-222° C. UV:e2JS = 9500. When mixed with the compound obtained by proceeding as indicated in example 1, the melting point of said compound is not lowered .
Eksempel 3. Example 3.
50 mg 2-klor-A<1->androsten-17p-ol-3-on, 0,2 ml pyridin og 0,1 ml acetanhydrid oppvarmes i 2 timer på dampbad. Den herved erholdte oppløsning røres inn i isvann. Der utfelles 2-klor-A<1->androsten-17p-ol-3-on-17-acetat. Væsken suges bort fra denne 50 mg of 2-chloro-A<1->androstene-17p-ol-3-one, 0.2 ml of pyridine and 0.1 ml of acetic anhydride are heated for 2 hours on a steam bath. The solution thus obtained is stirred into ice water. There, 2-chloro-A<1->androstene-17p-ol-3-one-17-acetate is precipitated. The liquid is sucked away from this
forbindelse og den omkrystalliseres fra isopropyleter. Den smelter ved 156° C. compound and it is recrystallized from isopropyl ether. It melts at 156°C.
Eksempel 4. Example 4.
1,15 g A^androsten-np-ol-S-on opp-løses i 70 ml tetrahydrofuran. Oppløsnin-gen tilsettes ved —60° C 6,1 ml propionsyre som inneholder 312 mg klor. Man lar 1.15 g of A-androstene-np-ol-S-one are dissolved in 70 ml of tetrahydrofuran. At -60° C., 6.1 ml of propionic acid containing 312 mg of chlorine is added to the solution. One lets
oppløsningen stå ved nevnte temperatur i 6 timer i mørke, hvorpå man rører den inn i isvann. Den vandige oppløsning ekstraheres derpå flere ganger med metylenklorid. Metylenkloridekstraktet vaskes let the solution stand at the mentioned temperature for 6 hours in the dark, after which it is stirred into ice water. The aqueous solution is then extracted several times with methylene chloride. The methylene chloride extract is washed
med natriumbikarbonatoppløsning og derpå med vann. Etter tørring over natriumsulfat inndampes ekstraktet til tørrhet i with sodium bicarbonate solution and then with water. After drying over sodium sulphate, the extract is evaporated to dryness in
vakuum. Residuet tas opp i 6 ml pyridin. vacuum. The residue is taken up in 6 ml of pyridine.
Etter 19 timers henstand fortynnes blan-dingen med eter, vaskes med 2 N saltsyre og derpå med vann. Oppløsningen i eter tørres over natriumsulfat og inndampes. Residuet omkrystalliseres fra eddikester. Man får 800 mg 2-klor-A^androstan-17-p-ol-3-on med smeltepunkt 221—222° C. UV:e„s = 9500. After standing for 19 hours, the mixture is diluted with ether, washed with 2 N hydrochloric acid and then with water. The solution in ether is dried over sodium sulfate and evaporated. The residue is recrystallized from acetic acid. 800 mg of 2-chloro-A^androstan-17-p-ol-3-one with melting point 221-222° C. UV:e„s = 9500 is obtained.
Eksempel 5. Example 5.
639 mg l-metyl-A^androsten-np-ol-3-on oppløses i 38 ml tetrahydrofuran og oppløsningen avkjøles til •—60° C. Den tilsettes derpå 165 mg klor i 1,9 ml propionsyre. Man lar blandingens temperatur stige til —32° C i løpet av 6 timer, hvorpå man rører oppløsningen inn i isvann. Blandin-gen ekstraheres med metylenklorid, metylenkloridekstraktet vaskes med natriumbi-karbonatoppløsning og derpå med vann. Ekstraktet inndampes til tørrhet i vakuum og man lar residuet stå natten over ved romtemperatur i 4 ml pyridin. Blan-dingen fortynnes derpå med vann og vaskes med fortynnet saltsyre samt med vann. Oppløsningen i eter tørres over natriumsulfat, inndampes til tørrhet i vakuum og residuet kromatograferes over silikagel. Ved eluering med like deler av tetraklor-kullstoff og metylenklorid får man 2-klor-l-metyl-A'-androsten-17(3-ol-3-on, som smelter ved 156—157° C etter omkrystallisasjon fra isopropyleter. UV:e90,, <=> 2180 £2,7 = 10 360. 639 mg of 1-methyl-α-androstene-np-ol-3-one are dissolved in 38 ml of tetrahydrofuran and the solution is cooled to -60° C. 165 mg of chlorine in 1.9 ml of propionic acid are then added. The temperature of the mixture is allowed to rise to -32° C over the course of 6 hours, after which the solution is stirred into ice water. The mixture is extracted with methylene chloride, the methylene chloride extract is washed with sodium bicarbonate solution and then with water. The extract is evaporated to dryness in vacuo and the residue is allowed to stand overnight at room temperature in 4 ml of pyridine. The mixture is then diluted with water and washed with dilute hydrochloric acid and water. The solution in ether is dried over sodium sulphate, evaporated to dryness in vacuo and the residue is chromatographed over silica gel. Elution with equal parts of carbon tetrachloride and methylene chloride gives 2-chloro-1-methyl-A'-androsten-17(3-ol-3-one), which melts at 156-157° C after recrystallization from isopropyl ether. UV :e90,, <=> 2180 £2.7 = 10,360.
Eksempel 6. Example 6.
302 mg 17p-metyl-AI<->androsten-17iP-ol-3-on i 15 ml tetrahydrofuran omsettes således som beskrevet i eksempel 5 med 78 mg klor i 1 ml propionsyre, opparbeides, behandles med 1,5 ml pyridin og opparbeides videre. Man får 2-klor-17a-metyl-A^androsten-np-ol-S-on som etter omkrystallisasjon fra isopropyleter smelter ved 167—168° C. UV:e=17 = 9100. 302 mg of 17β-methyl-Al<->androsten-17β-ol-3-one in 15 ml of tetrahydrofuran are thus reacted as described in example 5 with 78 mg of chlorine in 1 ml of propionic acid, worked up, treated with 1.5 ml of pyridine and worked up further. 2-Chloro-17a-methyl-A^androstene-np-ol-S-one is obtained which, after recrystallization from isopropyl ether, melts at 167-168° C. UV:e=17 = 9100.
Eksempel 7. Example 7.
276 mg nor-A'-androsten-17|3-ol-3-on 276 mg of nor-A'-androstene-17|3-ol-3-one
(smeltepunkt 146—147° C, UV:E22» = 10 650) (melting point 146-147° C, UV:E22" = 10,650)
oppløses i 10 ml tetrahydrofuran og omsettes med 78 mg klor i 1 mol propionsyre, således som beskrevet i eksempel 5, opparbeides og behandles videre med 3 ml pyridin samt opparbeides ytterligere. Produk-tet omkrystalliseres fra isopropyleter. Man får 2-klor-19-nor-A<1->androsten-17p-ol-3-on som melter ved 145—146° C. UV:eM = 9580. dissolved in 10 ml of tetrahydrofuran and reacted with 78 mg of chlorine in 1 mol of propionic acid, thus as described in example 5, worked up and treated further with 3 ml of pyridine and further worked up. The product is recrystallized from isopropyl ether. 2-chloro-19-nor-A<1->androstene-17p-ol-3-one is obtained which melts at 145-146° C. UV:eM = 9580.
Eksempel 8. Example 8.
350 mg 2-klor-A<1->androsten-17p-ol-3-on, 1,4 ml pyridin og 0,7 ml cyklopentyl-propionsyreanhydrid oppvarmes i 3 timer 350 mg of 2-chloro-A<1->androstene-17p-ol-3-one, 1.4 ml of pyridine and 0.7 ml of cyclopentyl propionic anhydride are heated for 3 hours
til 125° C og destilleres deretter i y2 time med vanndamp. Materialet ekstraheres derpå med metylenklorid. Metylenkloridekstraktet vaskes med vann, tørres over natriumsulfat og inndampes i vakuum til tørrhet. Det erholdte residuum omkrystalliseres fra hexan. Man får 2-klor-A<1->androsten-17p-ol-3-on- 17 -cyklopentylenpro-pionat som smelter ved 95,5—96,5° C. UV:£„; = 9350. to 125° C and then distilled for y2 hours with steam. The material is then extracted with methylene chloride. The methylene chloride extract is washed with water, dried over sodium sulphate and evaporated in vacuo to dryness. The residue obtained is recrystallized from hexane. 2-chloro-A<1->androstene-17p-ol-3-one-17-cyclopentylenepropionate is obtained which melts at 95.5-96.5° C. UV:£„; = 9350.
Eksempel 9. Example 9.
200 mg 2-klor-A<1->androsten-17p-ol-3-on suspenderes i 0,6 ml pyridin og 0,8 ml dioxan. Suspensjonen tilsettes under av-kjøling med is 0,12 ml benzoylklorid. Man lar den erholdte oppløsning stå 48 timer ved romtemperatur, hvorpå man rører den inn i isvann. Det utfelles 2-klor-A<1->androsten-17p-ol-3-on-17-benzoat. Væsken suges bort fra denne forbindelse og den omkrystalliseres fra eddikester. Forbindelsens smeltepunkt er 221,5—222,5° C. UV: gM = 8730 200 mg of 2-chloro-A<1->androstene-17p-ol-3-one are suspended in 0.6 ml of pyridine and 0.8 ml of dioxane. The suspension is added while cooling with ice 0.12 ml of benzoyl chloride. The resulting solution is allowed to stand for 48 hours at room temperature, after which it is stirred into ice water. 2-chloro-A<1->androstene-17p-ol-3-one-17-benzoate is precipitated. The liquid is sucked away from this compound and it is recrystallized from acetic acid. The compound's melting point is 221.5-222.5° C. UV: gM = 8730
e,:„ = 20142 e,:„ = 20142
e,„s = 11830 e,„s = 11830
= 2000 = 2000
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DK228471AA DK128412B (en) | 1971-05-12 | 1971-05-12 | Mineral wool mat for heat and cold insulation. |
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NO132939B true NO132939B (en) | 1975-10-27 |
NO132939C NO132939C (en) | 1976-02-04 |
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BE (1) | BE783379A (en) |
CH (1) | CH537807A (en) |
DE (1) | DE2223101C3 (en) |
DK (1) | DK128412B (en) |
ES (1) | ES402663A1 (en) |
FI (1) | FI55983C (en) |
FR (1) | FR2137805B1 (en) |
GB (1) | GB1386018A (en) |
IT (1) | IT955420B (en) |
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CA2166166C (en) † | 1995-01-12 | 2006-07-18 | Roy E. Shaffer | Insulation assembly and method for applying adhesive thereto |
NL1011603C2 (en) * | 1999-03-19 | 2000-09-27 | Rockwool Lapinus Bv | Self-adhesive insulation blanket. |
-
1971
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1972
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- 1972-05-09 FI FI1312/72A patent/FI55983C/en active
- 1972-05-09 GB GB2154772A patent/GB1386018A/en not_active Expired
- 1972-05-10 NO NO1651/72A patent/NO132939C/no unknown
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- 1972-05-10 IT IT24206/72A patent/IT955420B/en active
- 1972-05-12 NL NLAANVRAGE7206406,A patent/NL169909C/en not_active IP Right Cessation
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DK128412B (en) | 1974-04-29 |
NL169909B (en) | 1982-04-01 |
SE388164B (en) | 1976-09-27 |
FR2137805A1 (en) | 1972-12-29 |
AT314411B (en) | 1974-04-10 |
NO132939C (en) | 1976-02-04 |
GB1386018A (en) | 1975-03-05 |
DE2223101B2 (en) | 1980-01-17 |
NL169909C (en) | 1982-09-01 |
DE2223101C3 (en) | 1980-09-11 |
NL7206406A (en) | 1972-11-14 |
DE2223101A1 (en) | 1973-01-25 |
FI55983B (en) | 1979-07-31 |
IT955420B (en) | 1973-09-29 |
ES402663A1 (en) | 1975-04-01 |
FR2137805B1 (en) | 1976-08-06 |
FI55983C (en) | 1979-11-12 |
BE783379A (en) | 1972-09-01 |
CH537807A (en) | 1973-06-15 |
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