CA1106837A - Acides androstadiene-17-carboxyliques - Google Patents

Acides androstadiene-17-carboxyliques

Info

Publication number: CA1106837A
Authority: CA; Canada
Prior art keywords: hydroxyl group; formula; chlorine; group; compound
Prior art date: 1976-02-24
Legal status (The legal status 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 status listed.): Expired

Application number

CA353,029A

Other languages

English (en)

Inventor

Jaroslav Kalvoda

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Novartis AG

Original Assignee

Ciba Geigy Investments Ltd

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.)

1976-02-24

Filing date

1980-05-29

Publication date

1981-08-11

1976-02-24 Priority claimed from CH225376A external-priority patent/CH628355A5/de

1980-05-29 Application filed by Ciba Geigy Investments Ltd filed Critical Ciba Geigy Investments Ltd

1980-05-29 Priority to CA353,029A priority Critical patent/CA1106837A/fr

1981-08-11 Application granted granted Critical

1981-08-11 Publication of CA1106837A publication Critical patent/CA1106837A/fr

Status Expired legal-status Critical Current

Links

JMDKZCFWCUZPPB-SWAWSRFWSA-N (8r,9s,10s,13s)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12-decahydro-1h-cyclopenta[a]phenanthrene-17-carboxylic acid Chemical class C([C@H]12)CC3CCCC[C@]3(C)[C@H]1CC[C@@]1(C)C2=CC=C1C(O)=O JMDKZCFWCUZPPB-SWAWSRFWSA-N 0.000 title claims abstract description 5
239000000460 chlorine Substances 0.000 claims abstract description 37
229910052801 chlorine Inorganic materials 0.000 claims abstract description 35
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 28
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 22
238000000034 method Methods 0.000 claims abstract description 21
239000002253 acid Substances 0.000 claims abstract description 16
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 13
229910052731 fluorine Chemical group 0.000 claims abstract description 11
239000011737 fluorine Chemical group 0.000 claims abstract description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 8
239000001257 hydrogen Substances 0.000 claims abstract description 7
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 6
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 6
150000001735 carboxylic acids Chemical class 0.000 claims abstract description 4
238000004519 manufacturing process Methods 0.000 claims abstract description 4
125000001424 substituent group Chemical group 0.000 claims abstract description 3
150000001875 compounds Chemical class 0.000 claims description 13
-1 propionyloxy Chemical group 0.000 claims description 11
239000007858 starting material Substances 0.000 claims description 11
KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 claims description 7
150000003839 salts Chemical class 0.000 claims description 7
150000007513 acids Chemical class 0.000 claims description 5
125000001309 chloro group Chemical group Cl* 0.000 claims description 4
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 4
MEPYQKAEPRHALR-YFWFAHHUSA-N 1-[(8s,9s,10r,13s,14s,17s)-10,13-dimethyl-6,7,8,9,11,12,14,15,16,17-decahydro-3h-cyclopenta[a]phenanthren-17-yl]-2-hydroxyethanone Chemical class C1C=C[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 MEPYQKAEPRHALR-YFWFAHHUSA-N 0.000 claims description 3
PNYYBUOBTVHFDN-UHFFFAOYSA-N sodium bismuthate Chemical compound [Na+].[O-][Bi](=O)=O PNYYBUOBTVHFDN-UHFFFAOYSA-N 0.000 claims description 2
125000001153 fluoro group Chemical group F* 0.000 claims 2
239000000543 intermediate Substances 0.000 abstract description 3
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 abstract 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
239000000243 solution Substances 0.000 description 16
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 10
238000006243 chemical reaction Methods 0.000 description 10
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
239000002585 base Substances 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
238000007792 addition Methods 0.000 description 8
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
239000002904 solvent Substances 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
238000005660 chlorination reaction Methods 0.000 description 6
150000008064 anhydrides Chemical class 0.000 description 5
239000000203 mixture Substances 0.000 description 5
150000001408 amides Chemical class 0.000 description 4
239000003153 chemical reaction reagent Substances 0.000 description 4
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
230000032050 esterification Effects 0.000 description 4
238000005886 esterification reaction Methods 0.000 description 4
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 3
239000003377 acid catalyst Substances 0.000 description 3
229910052783 alkali metal Inorganic materials 0.000 description 3
150000001340 alkali metals Chemical class 0.000 description 3
150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
238000007033 dehydrochlorination reaction Methods 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
238000007127 saponification reaction Methods 0.000 description 3
238000003797 solvolysis reaction Methods 0.000 description 3
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 2
JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
150000007933 aliphatic carboxylic acids Chemical class 0.000 description 2
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 description 2
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
150000002009 diols Chemical class 0.000 description 2
125000004185 ester group Chemical group 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
125000000623 heterocyclic group Chemical group 0.000 description 2
235000011167 hydrochloric acid Nutrition 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
150000004679 hydroxides Chemical class 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 2
235000019260 propionic acid Nutrition 0.000 description 2
125000006239 protecting group Chemical group 0.000 description 2
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 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 2
ISNWPDWXSHAYEL-KTORGGLSSA-N (6s,8s,9s,10r,13s,14s,17s)-17-acetyl-6,10,13-trimethyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-one Chemical compound C([C@@]12C)=CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](C(C)=O)CC[C@H]21 ISNWPDWXSHAYEL-KTORGGLSSA-N 0.000 description 1
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
DRTQHJPVMGBUCF-UCVXFZOQSA-N 1-[(2s,3s,4s,5s)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione Chemical compound O[C@H]1[C@H](O)[C@H](CO)O[C@@H]1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-UCVXFZOQSA-N 0.000 description 1
YCPXWRQRBFJBPZ-UHFFFAOYSA-N 5-sulfosalicylic acid Chemical compound OC(=O)C1=CC(S(O)(=O)=O)=CC=C1O YCPXWRQRBFJBPZ-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
KJLLJBVWJUFUTE-RVPRXVRWSA-N O=C1C=C2CC[C@H]3[C@@H]4CCC([C@@]4(C)CC[C@@H]3[C@]2(C=C1)C)C(=O)OC Chemical compound O=C1C=C2CC[C@H]3[C@@H]4CCC([C@@]4(C)CC[C@@H]3[C@]2(C=C1)C)C(=O)OC KJLLJBVWJUFUTE-RVPRXVRWSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
229910001514 alkali metal chloride Inorganic materials 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
AKUJBENLRBOFTD-QZIXMDIESA-N betamethasone acetate Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)COC(C)=O)(O)[C@@]1(C)C[C@@H]2O AKUJBENLRBOFTD-QZIXMDIESA-N 0.000 description 1
MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical compound C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
239000012320 chlorinating reagent Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
150000004292 cyclic ethers Chemical class 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
238000006704 dehydrohalogenation reaction Methods 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical group 0.000 description 1
238000007038 hydrochlorination reaction Methods 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
150000003949 imides Chemical class 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
239000000155 melt Substances 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
125000000962 organic group Chemical group 0.000 description 1
125000001477 organic nitrogen group Chemical group 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
235000011007 phosphoric acid Nutrition 0.000 description 1
150000003016 phosphoric acids Chemical class 0.000 description 1
TZLVRPLSVNESQC-UHFFFAOYSA-N potassium azide Chemical compound [K+].[N-]=[N+]=[N-] TZLVRPLSVNESQC-UHFFFAOYSA-N 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
229940093956 potassium carbonate Drugs 0.000 description 1
235000011181 potassium carbonates Nutrition 0.000 description 1
WFIZEGIEIOHZCP-UHFFFAOYSA-M potassium formate Chemical compound [K+].[O-]C=O WFIZEGIEIOHZCP-UHFFFAOYSA-M 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
239000012266 salt solution Substances 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
150000003431 steroids Chemical class 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
239000000725 suspension Substances 0.000 description 1
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
PNQBEPDZQUOCNY-UHFFFAOYSA-N trifluoroacetyl chloride Chemical compound FC(F)(F)C(Cl)=O PNQBEPDZQUOCNY-UHFFFAOYSA-N 0.000 description 1

Landscapes

Steroid Compounds (AREA)

CA353,029A 1976-02-24 1980-05-29 Acides androstadiene-17-carboxyliques Expired CA1106837A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA353,029A CA1106837A (fr)	1976-02-24	1980-05-29	Acides androstadiene-17-carboxyliques

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
CH2253/76		1976-02-24
CH225376A CH628355A5 (de)	1976-02-24	1976-02-24	Verfahren zur herstellung neuer androstadien-17beta-carbonsaeuren und ihrer ester und salze.
CA272,291A CA1084483A (fr)	1976-02-24	1977-02-22	Esters d'acides androstadiene-17-carboxyliques
CA353,029A CA1106837A (fr)	1976-02-24	1980-05-29	Acides androstadiene-17-carboxyliques

Publications (1)

Publication Number	Publication Date
CA1106837A true CA1106837A (fr)	1981-08-11

Family

ID=27164923

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA353,029A Expired CA1106837A (fr)	1976-02-24	1980-05-29	Acides androstadiene-17-carboxyliques

Country Status (1)

Country	Link
CA (1)	CA1106837A (fr)

1980
- 1980-05-29 CA CA353,029A patent/CA1106837A/fr not_active Expired

Legal Events

Date	Code	Title	Description
1998-08-11	MKEX	Expiry

Publication	Publication Date	Title
CA1084483A (fr)	1980-08-26	Esters d'acides androstadiene-17-carboxyliques
KR100787293B1 (ko)	2007-12-20	중간물인 6.알파.,9.알파.-디플루오로-11.베타.,17.알파.-디히드록시-16.알파.-메틸-안드로스트-1,4-디엔-3-온 17.베타.-카르복실산을 제조하기 위한 산화 방법
US4650610A (en)	1987-03-17	Androstane carbothioic acids
KR100312269B1 (ko)	2002-05-13	6알파,9알파-디플루오르화스테로이드의신규제조방법및중간체
US5434258A (en)	1995-07-18	δ1,4 -pregnadiene-3,20-diones
US4525303A (en)	1985-06-25	Process for preparation of steroids
KR100312268B1 (ko)	2002-06-20	프레그난의신규17,20-에폭시드유도체,그의제조방법,코르티손유도체의제조에있어서의그의용도및중간체
KR920005830B1 (ko)	1992-07-20	아미노히드록시 세팜 카르복실레이트의 제조방법
US20030181742A1 (en)	2003-09-25	Process for the preparation of pregnane derivatives
US20050090675A1 (en)	2005-04-28	Process for preparing highly pure androstane 17-beta-carboxylic acids and 17-beta-carbothioic acid fluoromethyl esters thereof
KR100284824B1 (ko)	2001-03-15	16알파-메틸화 스테로이드의 제조 방법
CZ191398A3 (cs)	1998-11-11	Způsob přípravy 9,11ß-epoxisteroidů
NO137994B (no)	1978-02-27	Fremgangsm}te for behandling av en stangformet gjenstand for } beskytte dens ytre overflate
FI77445B (fi)	1988-11-30	Foerfarande foer framstaellning av ett indolderivat.
US4031080A (en)	1977-06-21	16-Alpha-methyl-17 alpha-bromo-1,4-pregnadiene-21-ol-3,20-dione-derivatives
EP0948491B1 (fr)	2004-01-21	Derives d'aminothiazole utiles dans la preparation d'antibiotiques a base de lactame
CA1306743C (fr)	1992-08-25	Double ester de derives 16-ethylestran-17-o1
US4323512A (en)	1982-04-06	Process for the preparation of steroidal 17α-arylcarboxylates
KR100394203B1 (ko)	2003-10-10	17베타-카르복시스테로이드유도체의제조방법및신규한중간체
US5602248A (en)	1997-02-11	Process for preparation of 9α-chloro-11β-formyloxypregna-3,20-diones
KR900001854B1 (ko)	1990-03-24	세펨유도체의 제조방법
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