SU946404A3 - Способ получени стероидных (16 @ ,17 @ )-циклогексен-или нафталин-21-карбоновых кислот или их сложных эфиров - Google Patents

Способ получени стероидных (16 @ ,17 @ )-циклогексен-или нафталин-21-карбоновых кислот или их сложных эфиров Download PDF

Info

Publication number: SU946404A3
Authority: SU; USSR - Soviet Union
Prior art keywords: hydrogen; mixture; chloroform; naphthalene; fluoro
Prior art date: 1978-06-26

Application number

SU792781351A

Other languages

English (en)

Russian (ru)

Inventor

Каннадиковилаком Варма Рави

Original Assignee

Е.Р.Сквибб Энд Санз,Инс (Фирма)

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.)

1978-06-26

Filing date

1979-06-25

Publication date

1982-07-23

1978-06-26 Priority claimed from US05/919,006 external-priority patent/US4160772A/en

1978-06-26 Priority claimed from US05/919,020 external-priority patent/US4164504A/en

1979-06-25 Application filed by Е.Р.Сквибб Энд Санз,Инс (Фирма) filed Critical Е.Р.Сквибб Энд Санз,Инс (Фирма)

1982-07-23 Application granted granted Critical

1982-07-23 Publication of SU946404A3 publication Critical patent/SU946404A3/ru

Links

150000003431 steroids Chemical class 0.000 title claims abstract description 11
150000002148 esters Chemical class 0.000 title claims description 4
238000000034 method Methods 0.000 title claims description 4
150000001875 compounds Chemical class 0.000 claims abstract description 20
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 14
239000001257 hydrogen Substances 0.000 claims abstract description 14
125000000217 alkyl group Chemical group 0.000 claims abstract description 6
229910052731 fluorine Chemical group 0.000 claims abstract description 5
239000011737 fluorine Chemical group 0.000 claims abstract description 5
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims abstract description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 5
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 3
125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims abstract 2
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 48
239000000203 mixture Substances 0.000 claims description 46
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 29
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 20
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 16
NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 claims description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
238000006243 chemical reaction Methods 0.000 claims description 6
NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 claims description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 3
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 2
230000032050 esterification Effects 0.000 claims description 2
238000005886 esterification reaction Methods 0.000 claims description 2
238000005809 transesterification reaction Methods 0.000 claims description 2
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims 1
229910052802 copper Inorganic materials 0.000 claims 1
239000010949 copper Substances 0.000 claims 1
150000002431 hydrogen Chemical group 0.000 claims 1
125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 8
229910052736 halogen Chemical group 0.000 abstract 2
150000002367 halogens Chemical group 0.000 abstract 2
125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
125000003545 alkoxy group Chemical group 0.000 abstract 1
125000004448 alkyl carbonyl group Chemical group 0.000 abstract 1
230000003110 anti-inflammatory effect Effects 0.000 abstract 1
125000003118 aryl group Chemical group 0.000 abstract 1
229910052801 chlorine Inorganic materials 0.000 abstract 1
239000000460 chlorine Substances 0.000 abstract 1
125000001309 chloro group Chemical group Cl* 0.000 abstract 1
125000004093 cyano group Chemical group *C#N 0.000 abstract 1
239000000543 intermediate Substances 0.000 abstract 1
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 70
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 47
239000000243 solution Substances 0.000 description 33
OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 31
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
239000002253 acid Substances 0.000 description 24
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 15
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
239000000047 product Substances 0.000 description 13
239000000741 silica gel Substances 0.000 description 11
229910002027 silica gel Inorganic materials 0.000 description 11
239000007787 solid Substances 0.000 description 10
238000002425 crystallisation Methods 0.000 description 9
230000008025 crystallization Effects 0.000 description 9
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 8
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
229960000583 acetic acid Drugs 0.000 description 7
239000000725 suspension Substances 0.000 description 7
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
GOPYZMJAIPBUGX-UHFFFAOYSA-N [O-2].[O-2].[Mn+4] Chemical class [O-2].[O-2].[Mn+4] GOPYZMJAIPBUGX-UHFFFAOYSA-N 0.000 description 6
238000000354 decomposition reaction Methods 0.000 description 6
238000001704 evaporation Methods 0.000 description 6
230000008020 evaporation Effects 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 5
238000010828 elution Methods 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
229910052943 magnesium sulfate Inorganic materials 0.000 description 5
235000019341 magnesium sulphate Nutrition 0.000 description 5
238000010992 reflux Methods 0.000 description 5
239000002904 solvent Substances 0.000 description 5
238000003756 stirring Methods 0.000 description 5
238000004809 thin layer chromatography Methods 0.000 description 5
238000005406 washing Methods 0.000 description 5
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 4
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
235000019270 ammonium chloride Nutrition 0.000 description 4
HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 4
239000012362 glacial acetic acid Substances 0.000 description 4
150000004702 methyl esters Chemical class 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
239000000126 substance Substances 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
239000005909 Kieselgur Substances 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 3
WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 3
239000012299 nitrogen atmosphere Substances 0.000 description 3
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
239000007858 starting material Substances 0.000 description 3
201000004624 Dermatitis Diseases 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
239000012267 brine Substances 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
239000012141 concentrate Substances 0.000 description 2
NWFNSTOSIVLCJA-UHFFFAOYSA-L copper;diacetate;hydrate Chemical compound O.[Cu+2].CC([O-])=O.CC([O-])=O NWFNSTOSIVLCJA-UHFFFAOYSA-L 0.000 description 2
YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 2
238000002845 discoloration Methods 0.000 description 2
125000004494 ethyl ester group Chemical group 0.000 description 2
239000012535 impurity Substances 0.000 description 2
239000000463 material Substances 0.000 description 2
KPSSIOMAKSHJJG-UHFFFAOYSA-N neopentyl alcohol Chemical compound CC(C)(C)CO KPSSIOMAKSHJJG-UHFFFAOYSA-N 0.000 description 2
235000011007 phosphoric acid Nutrition 0.000 description 2
DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
238000012746 preparative thin layer chromatography Methods 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 2
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
CHHASAIQKXOAOX-UHFFFAOYSA-N 1-(2,2-dimethylpropoxy)-2,2-dimethylpropane Chemical compound CC(C)(C)COCC(C)(C)C CHHASAIQKXOAOX-UHFFFAOYSA-N 0.000 description 1
JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 1
CSDQQAQKBAQLLE-UHFFFAOYSA-N 4-(4-chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound C1=CC(Cl)=CC=C1C1C(C=CS2)=C2CCN1 CSDQQAQKBAQLLE-UHFFFAOYSA-N 0.000 description 1
102000007469 Actins Human genes 0.000 description 1
108010085238 Actins Proteins 0.000 description 1
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Natural products CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
201000009053 Neurodermatitis Diseases 0.000 description 1
-1 Octyl ester Chemical class 0.000 description 1
208000003251 Pruritus Diseases 0.000 description 1
201000004681 Psoriasis Diseases 0.000 description 1
206010042496 Sunburn Diseases 0.000 description 1
150000001241 acetals Chemical class 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
239000000538 analytical sample Substances 0.000 description 1
229940121363 anti-inflammatory agent Drugs 0.000 description 1
239000002260 anti-inflammatory agent Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
208000010668 atopic eczema Diseases 0.000 description 1
239000001110 calcium chloride Substances 0.000 description 1
229910001628 calcium chloride Inorganic materials 0.000 description 1
239000002026 chloroform extract Substances 0.000 description 1
SKCNIGRBPJIUBQ-UHFFFAOYSA-N chloroform;ethyl acetate Chemical compound ClC(Cl)Cl.CCOC(C)=O SKCNIGRBPJIUBQ-UHFFFAOYSA-N 0.000 description 1
239000012043 crude product Substances 0.000 description 1
WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000000284 extract Substances 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000012065 filter cake Substances 0.000 description 1
239000006260 foam Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
230000007803 itching Effects 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
229910052748 manganese Inorganic materials 0.000 description 1
239000011572 manganese Substances 0.000 description 1
230000008018 melting Effects 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
150000003016 phosphoric acids Chemical class 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000002002 slurry Substances 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
DGPIGKCOQYBCJH-UHFFFAOYSA-M sodium;acetic acid;hydroxide Chemical compound O.[Na+].CC([O-])=O DGPIGKCOQYBCJH-UHFFFAOYSA-M 0.000 description 1
239000012265 solid product Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J53/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by condensation with a carbocyclic rings or by formation of an additional ring by means of a direct link between two ring carbon atoms, including carboxyclic rings fused to the cyclopenta(a)hydrophenanthrene skeleton are included in this class
- C07J53/002—Carbocyclic rings fused
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J13/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having a carbon-to-carbon double bond from or to position 17
- C07J13/005—Normal steroids containing carbon, hydrogen, halogen or oxygen having a carbon-to-carbon double bond from or to position 17 with double bond in position 16 (17)

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Rheumatology (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
Animal Behavior & Ethology (AREA)
Pain & Pain Management (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Steroid Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

SU792781351A 1978-06-26 1979-06-25 Способ получени стероидных (16 @ ,17 @ )-циклогексен-или нафталин-21-карбоновых кислот или их сложных эфиров SU946404A3 (ru)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US05/919,006 US4160772A (en)	1978-06-26	1978-06-26	Steroidal[16α,17-d]cyclohexene-21-carboxylic acid esters
US05/919,020 US4164504A (en)	1978-06-26	1978-06-26	Steroidal[16α,17-b]naphthaleno-21-carboxylic acid esters

Publications (1)

Publication Number	Publication Date
SU946404A3 true SU946404A3 (ru)	1982-07-23

Family

ID=27129763

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
SU792781351A SU946404A3 (ru)	1978-06-26	1979-06-25	Способ получени стероидных (16 @ ,17 @ )-циклогексен-или нафталин-21-карбоновых кислот или их сложных эфиров
SU802995671A SU1055334A3 (ru)	1978-06-26	1980-10-23	Способ получени стероидных /16 @ ,17 @ /-циклогексен-21-карбоновых кислот или их эфиров

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
SU802995671A SU1055334A3 (ru)	1978-06-26	1980-10-23	Способ получени стероидных /16 @ ,17 @ /-циклогексен-21-карбоновых кислот или их эфиров

Country Status (24)

Country	Link
AU (1)	AU524173B2 (de)
CA (1)	CA1142916A (de)
CH (1)	CH642087A5 (de)
CS (2)	CS208159B2 (de)
DD (1)	DD144550A5 (de)
DE (1)	DE2925552A1 (de)
DK (1)	DK267079A (de)
ES (2)	ES481875A1 (de)
FI (1)	FI791934A7 (de)
FR (1)	FR2429796A1 (de)
GB (2)	GB2023608B (de)
GR (1)	GR72244B (de)
HU (1)	HU180089B (de)
IE (1)	IE49178B1 (de)
IL (1)	IL57622A (de)
IT (1)	IT1162746B (de)
LU (1)	LU81420A1 (de)
NL (1)	NL7904510A (de)
NO (1)	NO792118L (de)
NZ (1)	NZ190510A (de)
PL (1)	PL216614A1 (de)
PT (1)	PT69818A (de)
SE (1)	SE7905568L (de)
SU (2)	SU946404A3 (de)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4391755A (en) *	1982-01-18	1983-07-05	E. R. Squibb & Sons, Inc.	Steroid monohydrates, formulations containing same and method

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2924307A (en) *	1956-09-27	1960-02-09	Gen Motors Corp	Brake adjusting device
US3944584A (en) *	1975-02-03	1976-03-16	E. R. Squibb & Sons, Inc.	Steroidal (16α,17-d)cyclohexenes

1979
- 1979-05-21 NZ NZ190510A patent/NZ190510A/xx unknown
- 1979-05-23 CA CA000328182A patent/CA1142916A/en not_active Expired
- 1979-05-25 GB GB7918394A patent/GB2023608B/en not_active Expired
- 1979-05-28 AU AU47481/79A patent/AU524173B2/en not_active Ceased
- 1979-05-29 GR GR59210A patent/GR72244B/el unknown
- 1979-06-07 FR FR7914578A patent/FR2429796A1/fr active Granted
- 1979-06-08 NL NL7904510A patent/NL7904510A/xx not_active Application Discontinuation
- 1979-06-15 CS CS794141A patent/CS208159B2/cs unknown
- 1979-06-15 CS CS799420A patent/CS208160B2/cs unknown
- 1979-06-18 FI FI791934A patent/FI791934A7/fi not_active Application Discontinuation
- 1979-06-22 IL IL57622A patent/IL57622A/xx unknown
- 1979-06-25 HU HU79SU1020A patent/HU180089B/hu unknown
- 1979-06-25 ES ES481875A patent/ES481875A1/es not_active Expired
- 1979-06-25 SU SU792781351A patent/SU946404A3/ru active
- 1979-06-25 NO NO792118A patent/NO792118L/no unknown
- 1979-06-25 IT IT23840/79A patent/IT1162746B/it active
- 1979-06-25 DE DE19792925552 patent/DE2925552A1/de not_active Withdrawn
- 1979-06-25 SE SE7905568A patent/SE7905568L/ not_active Application Discontinuation
- 1979-06-25 LU LU81420A patent/LU81420A1/xx unknown
- 1979-06-25 CH CH592479A patent/CH642087A5/de not_active IP Right Cessation
- 1979-06-25 ES ES481866A patent/ES481866A1/es not_active Expired
- 1979-06-25 DK DK267079A patent/DK267079A/da not_active Application Discontinuation
- 1979-06-26 DD DD79213895A patent/DD144550A5/de unknown
- 1979-06-26 PL PL21661479A patent/PL216614A1/xx unknown
- 1979-06-26 PT PT69818A patent/PT69818A/pt unknown
- 1979-08-08 IE IE1181/79A patent/IE49178B1/en unknown
1980
- 1980-10-23 SU SU802995671A patent/SU1055334A3/ru active
1982
- 1982-03-19 GB GB08208035A patent/GB2106116B/en not_active Expired

Also Published As

Publication number	Publication date
NZ190510A (en)	1982-03-09
DE2925552A1 (de)	1980-01-17
PL216614A1 (de)	1980-03-24
LU81420A1 (fr)	1979-09-12
CS208160B2 (en)	1981-08-31
PT69818A (en)	1979-07-01
GB2106116B (en)	1983-08-03
IE49178B1 (en)	1985-08-21
FR2429796A1 (fr)	1980-01-25
IT1162746B (it)	1987-04-01
IL57622A (en)	1983-02-23
AU524173B2 (en)	1982-09-02
CH642087A5 (de)	1984-03-30
DD144550A5 (de)	1980-10-22
GB2106116A (en)	1983-04-07
IE791181L (en)	1979-12-26
ES481866A1 (es)	1980-06-16
IT7923840A0 (it)	1979-06-25
CA1142916A (en)	1983-03-15
AU4748179A (en)	1980-01-03
DK267079A (da)	1979-12-27
NL7904510A (nl)	1979-12-28
FI791934A7 (fi)	1981-01-01
GB2023608B (en)	1983-04-27
GB2023608A (en)	1980-01-03
ES481875A1 (es)	1980-07-01
SU1055334A3 (ru)	1983-11-15
FR2429796B1 (de)	1983-01-07
SE7905568L (sv)	1979-12-27
GR72244B (de)	1983-10-04
NO792118L (no)	1979-12-28
IL57622A0 (en)	1979-10-31
CS208159B2 (en)	1981-08-31
HU180089B (en)	1983-01-28

Publication	Publication Date	Title
AU775831B2 (en)	2004-08-19	Process for preparing 17alpha-acetoxy-11beta-(4-N,N-(dimethylamino)phenyl)-21- methoxy-19-norpregna-4,9-diene-3,20-dione, intermediates useful in the process, and processes for preparing such intermediates
SU946404A3 (ru)	1982-07-23	Способ получени стероидных (16 @ ,17 @ )-циклогексен-или нафталин-21-карбоновых кислот или их сложных эфиров
US2900382A (en)	1959-08-18	Method of making delta4,6 steroid compounds from delta4 steroid compounds
GB1564807A (en)	1980-04-16	Cholestene derivatives
Murai et al.	1977	Rishitin. II. Synthesis.
DK171850B1 (da)	1997-07-07	Fremgangsmåde til fremstilling af 17alfa-ethynyl-17beta-hydroxy-18-methyl-4,15-østradien-3-on og mellemprodukter til anvendelse ved fremgangsmåden
SU656529A3 (ru)	1979-04-05	Способ получени -фторандростенов
US3847906A (en)	1974-11-12	Process for the manufacture of beta-(3-oxo-7alpha-acetylthio-17beta-hydroxy-4-androsten-17alpha-yl)-propionic acid gamma-lactone
SU615863A3 (ru)	1978-07-15	Способ получени производных прегнановой кислоты
US2926167A (en)	1960-02-23	Process of esterifying ib-hydroxy
US3812156A (en)	1974-05-21	Process for preparing lower alkyl flavone-7-oxyacetates
JPS645034B2 (de)	1989-01-27
US3272803A (en)	1966-09-13	2, 2-ethylenetestosterones
US2897214A (en)	1959-07-28	3-hydroxy-11-keto-delta22-ergostene and esters thereof
KR830001132B1 (ko)	1983-06-14	스테로이드 [16a, 17-b] 시클로헥센-21-카르복실산 및 그의 에스테르의 제조방법
SU679147A3 (ru)	1979-08-05	Способ получени правовращающих гомостероидов
US2847422A (en)	1958-08-12	Hydroxylated 2, 13-dimethyl-7, 9-dioxopolyhydrophenanthrene-1-propionic acid lactones and salts
US4160772A (en)	1979-07-10	Steroidal[16α,17-d]cyclohexene-21-carboxylic acid esters
SU1104134A1 (ru)	1984-07-23	Способ получени аналогов простагландинов @
US3331868A (en)	1967-07-18	A-nor-b-norsteroids and intermediates
US4164504A (en)	1979-08-14	Steroidal[16α,17-b]naphthaleno-21-carboxylic acid esters
US2852536A (en)	1958-09-16	Delta8-bisnorallocholenates
US3272797A (en)	1966-09-13	Cyclic acetals and ketals of the 6alpha-methylpregnane series and process for preparing same
JPH023798B2 (de)	1990-01-24
US3190895A (en)	1965-06-22	Substituted androstan-16alpha-ylacetic acids