FI90345B - Förfarande för kontroll av epimerdistributionen vid framställning av 16,17-acetaler av pregnanderivat - Google Patents

Förfarande för kontroll av epimerdistributionen vid framställning av 16,17-acetaler av pregnanderivat Download PDF

Info

Publication number: FI90345B
Authority: FI; Finland
Prior art keywords: reaction; epimer; catalyst; epimeric; hydrogen
Prior art date: 1986-09-25

Application number

FI874189A

Other languages

English (en)

Finnish (fi)

Other versions

FI90345C (sv

FI874189L (sv

FI874189A0 (sv

Inventor

Edib Jakupovic

Roy Torvald Sourander

Jan Urban Stenhede

Rolf Peter Svensson

Original Assignee

Astra Pharma Prod

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.)

1986-09-25

Filing date

1987-09-24

Publication date

1993-10-15

1987-09-24 Application filed by Astra Pharma Prod filed Critical Astra Pharma Prod

1987-09-24 Publication of FI874189A0 publication Critical patent/FI874189A0/sv

1988-03-26 Publication of FI874189L publication Critical patent/FI874189L/sv

1993-10-15 Application granted granted Critical

1993-10-15 Publication of FI90345B publication Critical patent/FI90345B/sv

1994-01-25 Publication of FI90345C publication Critical patent/FI90345C/sv

Links

238000009826 distribution Methods 0.000 title claims abstract description 31
238000000034 method Methods 0.000 title claims abstract description 29
238000002360 preparation method Methods 0.000 title claims abstract description 19
150000003126 pregnane derivatives Chemical class 0.000 title claims abstract description 10
238000006243 chemical reaction Methods 0.000 claims abstract description 76
239000003054 catalyst Substances 0.000 claims abstract description 27
150000002576 ketones Chemical class 0.000 claims abstract description 17
239000002904 solvent Substances 0.000 claims abstract description 15
239000002253 acid Substances 0.000 claims abstract description 12
239000000463 material Substances 0.000 claims abstract description 8
150000008282 halocarbons Chemical class 0.000 claims abstract description 7
229930195733 hydrocarbon Natural products 0.000 claims abstract description 6
150000002430 hydrocarbons Chemical class 0.000 claims abstract description 6
239000004215 Carbon black (E152) Substances 0.000 claims abstract description 5
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 104
239000000460 chlorine Substances 0.000 claims description 32
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 28
239000000203 mixture Substances 0.000 claims description 28
ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 claims description 26
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical group OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims description 23
150000001299 aldehydes Chemical class 0.000 claims description 20
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 18
150000001875 compounds Chemical class 0.000 claims description 18
NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 claims description 15
125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims description 15
JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 claims description 15
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 12
238000009472 formulation Methods 0.000 claims description 12
229910052739 hydrogen Inorganic materials 0.000 claims description 12
239000001257 hydrogen Substances 0.000 claims description 12
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 10
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
229910052801 chlorine Inorganic materials 0.000 claims description 9
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 8
229910052731 fluorine Inorganic materials 0.000 claims description 8
239000011737 fluorine Substances 0.000 claims description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
125000000217 alkyl group Chemical group 0.000 claims description 7
150000002009 diols Chemical class 0.000 claims description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
230000003197 catalytic effect Effects 0.000 claims description 6
150000002431 hydrogen Chemical class 0.000 claims description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
239000008187 granular material Substances 0.000 claims description 5
125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Substances CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 3
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
239000003377 acid catalyst Substances 0.000 claims description 2
238000006345 epimerization reaction Methods 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
239000002198 insoluble material Substances 0.000 claims description 2
229920006395 saturated elastomer Polymers 0.000 claims description 2
-1 steroid acetal Chemical class 0.000 claims description 2
150000003460 sulfonic acids Chemical class 0.000 claims description 2
241000282461 Canis lupus Species 0.000 claims 1
230000001404 mediated effect Effects 0.000 claims 1
239000012429 reaction media Substances 0.000 abstract description 3
BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 abstract 2
125000002485 formyl group Chemical class [H]C(*)=O 0.000 abstract 1
239000003607 modifier Substances 0.000 abstract 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
239000011541 reaction mixture Substances 0.000 description 28
238000004128 high performance liquid chromatography Methods 0.000 description 23
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 21
239000004576 sand Substances 0.000 description 19
239000000047 product Substances 0.000 description 17
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 16
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
239000002245 particle Substances 0.000 description 14
238000005160 1H NMR spectroscopy Methods 0.000 description 10
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
229910004298 SiO 2 Inorganic materials 0.000 description 10
229910000027 potassium carbonate Inorganic materials 0.000 description 9
QWOJMRHUQHTCJG-UHFFFAOYSA-N CC([CH2-])=O Chemical compound CC([CH2-])=O QWOJMRHUQHTCJG-UHFFFAOYSA-N 0.000 description 8
235000015320 potassium carbonate Nutrition 0.000 description 8
238000003756 stirring Methods 0.000 description 8
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 8
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
239000007795 chemical reaction product Substances 0.000 description 6
239000007787 solid Substances 0.000 description 6
239000000126 substance Substances 0.000 description 5
238000003420 transacetalization reaction Methods 0.000 description 5
SEKYBDYVXDAYPY-ILNISADRSA-N (8s,9s,10r,11s,13s,14s,16r,17s)-11,16,17-trihydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-7,8,9,11,12,14,15,16-octahydro-6h-cyclopenta[a]phenanthren-3-one Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@]([C@H](O)C4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 SEKYBDYVXDAYPY-ILNISADRSA-N 0.000 description 4
NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
238000001914 filtration Methods 0.000 description 4
FEBLZLNTKCEFIT-VSXGLTOVSA-N fluocinolone acetonide Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@]1(F)[C@@H]2[C@@H]2C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]2(C)C[C@@H]1O FEBLZLNTKCEFIT-VSXGLTOVSA-N 0.000 description 4
QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 description 4
230000035484 reaction time Effects 0.000 description 4
VOVIALXJUBGFJZ-KWVAZRHASA-N Budesonide Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1C[C@H]3OC(CCC)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@@H]2O VOVIALXJUBGFJZ-KWVAZRHASA-N 0.000 description 3
239000007832 Na2SO4 Substances 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
229960004436 budesonide Drugs 0.000 description 3
239000011162 core material Substances 0.000 description 3
238000002425 crystallisation Methods 0.000 description 3
230000008025 crystallization Effects 0.000 description 3
229960001347 fluocinolone acetonide Drugs 0.000 description 3
GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 3
238000002156 mixing Methods 0.000 description 3
210000005036 nerve Anatomy 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
229910052938 sodium sulfate Inorganic materials 0.000 description 3
235000011152 sodium sulphate Nutrition 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
239000000010 aprotic solvent Substances 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
238000004440 column chromatography Methods 0.000 description 2
229940124307 fluoroquinolone Drugs 0.000 description 2
230000006698 induction Effects 0.000 description 2
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
239000013618 particulate matter Substances 0.000 description 2
239000002243 precursor Substances 0.000 description 2
230000035935 pregnancy Effects 0.000 description 2
239000000725 suspension Substances 0.000 description 2
YNDXUCZADRHECN-JNQJZLCISA-N triamcinolone acetonide Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@@H]2O YNDXUCZADRHECN-JNQJZLCISA-N 0.000 description 2
229960002117 triamcinolone acetonide Drugs 0.000 description 2
VZRAKVPDZIQRGT-WZBAXQLOSA-N (8r,9s,10s,13r,14s,17r)-17-ethenyl-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthrene Chemical compound C1CCC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)C=C)[C@@H]4[C@@H]3CCC21 VZRAKVPDZIQRGT-WZBAXQLOSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
241000084978 Rena Species 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
240000008042 Zea mays Species 0.000 description 1
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
235000002017 Zea mays subsp mays Nutrition 0.000 description 1
238000006359 acetalization reaction Methods 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000033228 biological regulation Effects 0.000 description 1
238000004061 bleaching Methods 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
150000001728 carbonyl compounds Chemical class 0.000 description 1
WBLIXGSTEMXDSM-UHFFFAOYSA-N chloromethane Chemical compound Cl[CH2] WBLIXGSTEMXDSM-UHFFFAOYSA-N 0.000 description 1
238000013375 chromatographic separation Methods 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
235000005822 corn Nutrition 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
239000003337 fertilizer Substances 0.000 description 1
229940043075 fluocinolone Drugs 0.000 description 1
230000000855 fungicidal effect Effects 0.000 description 1
239000000417 fungicide Substances 0.000 description 1
QFWPJPIVLCBXFJ-UHFFFAOYSA-N glymidine Chemical compound N1=CC(OCCOC)=CN=C1NS(=O)(=O)C1=CC=CC=C1 QFWPJPIVLCBXFJ-UHFFFAOYSA-N 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
238000003384 imaging method Methods 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
QPJSUIGXIBEQAC-UHFFFAOYSA-N n-(2,4-dichloro-5-propan-2-yloxyphenyl)acetamide Chemical compound CC(C)OC1=CC(NC(C)=O)=C(Cl)C=C1Cl QPJSUIGXIBEQAC-UHFFFAOYSA-N 0.000 description 1
239000008188 pellet Substances 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
235000020079 raki Nutrition 0.000 description 1
238000011084 recovery Methods 0.000 description 1
230000008929 regeneration Effects 0.000 description 1
238000011069 regeneration method Methods 0.000 description 1
239000005871 repellent Substances 0.000 description 1
230000002940 repellent Effects 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
239000002002 slurry Substances 0.000 description 1
239000012265 solid product Substances 0.000 description 1
241000894007 species Species 0.000 description 1
239000008107 starch Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
150000003431 steroids Chemical class 0.000 description 1
238000011144 upstream manufacturing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
- C07J71/0005—Oxygen-containing hetero ring
- C07J71/0026—Oxygen-containing hetero ring cyclic ketals
- C07J71/0031—Oxygen-containing hetero ring cyclic ketals at positions 16, 17

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Steroid Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

FI874189A 1986-09-25 1987-09-24 Förfarande för kontroll av epimerdistributionen vid framställning av 16,17-acetaler av pregnanderivat FI90345C (sv)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
SE8604059A SE8604059D0 (sv)	1986-09-25	1986-09-25	A method of controlling the epimeric distribution in the preparation of 16,17-acetals of pregnane derivatives
SE8604059		1986-09-25

Publications (4)

Publication Number	Publication Date
FI874189A0 FI874189A0 (sv)	1987-09-24
FI874189L FI874189L (sv)	1988-03-26
FI90345B true FI90345B (sv)	1993-10-15
FI90345C FI90345C (sv)	1994-01-25

Family

ID=20365704

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
FI874189A FI90345C (sv)	1986-09-25	1987-09-24	Förfarande för kontroll av epimerdistributionen vid framställning av 16,17-acetaler av pregnanderivat

Country Status (13)

Country	Link
US (1)	US4925933A (sv)
EP (1)	EP0262108B1 (sv)
JP (1)	JP2668000B2 (sv)
KR (1)	KR950014460B1 (sv)
AT (1)	ATE70066T1 (sv)
CY (1)	CY1791A (sv)
DE (1)	DE3774987D1 (sv)
ES (1)	ES2026576T3 (sv)
FI (1)	FI90345C (sv)
GR (1)	GR3003332T3 (sv)
HK (1)	HK46194A (sv)
IL (1)	IL83994A (sv)
SE (1)	SE8604059D0 (sv)

Families Citing this family (20)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
SE8903219D0 (sv) *	1989-10-02	1989-10-02	Astra Ab	Process for the manufacture of budesonide
GR1001529B (el) *	1990-09-07	1994-03-31	Elmuquimica Farm Sl	Μέ?οδος για την λήψη νέων 21-εστέρων της 16-17-ακετάλης της πρ να-1,4-διενο-3,20-διόνης.
SE9100341D0 (sv) *	1991-02-04	1991-02-04	Astra Ab	Novel steroids
FR2675146A1 (fr) *	1991-04-10	1992-10-16	Roussel Uclaf	Nouveaux derives sterouides de la pregna-1,4-diene-3,20-dione, leur preparation, leur application a la preparation de derives 16,17-methylene dioxy substitues et nouveaux intermediaires.
GB9423919D0 (en) *	1994-11-26	1995-01-11	Rhone Poulenc Rorer Ltd	Chemical process
DE19635498A1 (de) *	1996-09-03	1998-03-26	Byk Gulden Lomberg Chem Fab	Verfahren zur Epimerenanreicherung
IT1291288B1 (it) *	1997-04-30	1999-01-07	Farmabios Srl	Processo per la preparazione di 16,17 acetali di derivati pregnanici con controllo della distribuzione epimerica al c-22.
US6266556B1 (en)	1998-04-27	2001-07-24	Beth Israel Deaconess Medical Center, Inc.	Method and apparatus for recording an electroencephalogram during transcranial magnetic stimulation
IT1302657B1 (it) *	1998-10-13	2000-09-29	Farmabios Srl	Processo stereoselettivo per la preparazione di budesonide nella formadi epimero 22-r.
KR20070116185A (ko) *	2000-11-10	2007-12-06	니코메드 게엠베하	트랜스케탈화 반응에 의한16,17-[(시클로헥실메틸렌)비스(옥시)]-11,21-디히드록시-프레그나-1,4-디엔-3,20-디온 또는 이의 21-이소부티라트의제조방법
WO2003027134A1 (en) *	2001-09-25	2003-04-03	Pharmacia & Upjohn Company	Stereoselective transacetalization of steroidal c-22 acetonide
AU2003291634A1 (en) *	2002-10-08	2004-05-04	Sepracor Inc.	Fatty acid modified forms of glucocorticoids and their use as anti-inflammatory
JP2009512733A (ja) *	2005-11-02	2009-03-26	シコールインコーポレイティド	シクレソニドの改良された製造法
US20070232578A1 (en) *	2006-02-15	2007-10-04	Pierluigi Rossetto	Crystalline forms of ciclesonide
US10233210B2 (en)	2015-01-30	2019-03-19	Coral Drugs Pvt. Ltd.	Process for preparation of glucocorticoid steroids
EP4659809A2 (en)	2016-11-08	2025-12-10	Regeneron Pharmaceuticals, Inc.	Steroids and protein-conjugates thereof
US11491237B2 (en)	2017-05-18	2022-11-08	Regeneron Pharmaceuticals, Inc.	Cyclodextrin protein drug conjugates
MX2020004691A (es)	2017-11-07	2020-08-20	Regeneron Pharma	Enlazadores hidrofilicos para conjugados anticuerpo-farmaco.
CN112004557B (zh)	2018-01-08	2024-07-30	里珍纳龙药品有限公司	类固醇类化合物及其抗体偶联物
KR20210008008A (ko)	2018-05-09	2021-01-20	리제너론 파마슈티칼스 인코포레이티드	항-msr1 항체 및 이의 사용 방법

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
SE378109B (sv) *	1972-05-19	1975-08-18	Bofors Ab
SE378110B (sv) *	1972-05-19	1975-08-18	Bofors Ab
SE8008524L (sv) *	1980-12-04	1982-06-05	Draco Ab	4-pregnen-derivat, ett forfarande for deras framstellning, beredning och metod for behandling av inflammatoriska tillstand
IT1196142B (it) *	1984-06-11	1988-11-10	Sicor Spa	Procedimento per la preparazione di 16,17-acetali di derivati pregnanici e nuovi composti ottenuti

1986
- 1986-09-25 SE SE8604059A patent/SE8604059D0/sv unknown
1987
- 1987-09-11 US US07/096,598 patent/US4925933A/en not_active Expired - Lifetime
- 1987-09-18 ES ES198787850282T patent/ES2026576T3/es not_active Expired - Lifetime
- 1987-09-18 EP EP87850282A patent/EP0262108B1/en not_active Expired - Lifetime
- 1987-09-18 AT AT87850282T patent/ATE70066T1/de not_active IP Right Cessation
- 1987-09-18 DE DE8787850282T patent/DE3774987D1/de not_active Expired - Fee Related
- 1987-09-23 IL IL83994A patent/IL83994A/xx unknown
- 1987-09-24 KR KR1019870010561A patent/KR950014460B1/ko not_active Expired - Fee Related
- 1987-09-24 FI FI874189A patent/FI90345C/sv not_active IP Right Cessation
- 1987-09-24 JP JP62237588A patent/JP2668000B2/ja not_active Expired - Fee Related
1991
- 1991-12-12 GR GR91401949T patent/GR3003332T3/el unknown
1994
- 1994-05-12 HK HK46194A patent/HK46194A/en not_active IP Right Cessation
1995
- 1995-10-20 CY CY179195A patent/CY1791A/xx unknown

Also Published As

Publication number	Publication date
US4925933A (en)	1990-05-15
FI90345C (sv)	1994-01-25
CY1791A (en)	1995-10-20
EP0262108B1 (en)	1991-12-04
JP2668000B2 (ja)	1997-10-27
EP0262108A1 (en)	1988-03-30
KR880003969A (ko)	1988-06-01
IL83994A0 (en)	1988-02-29
SE8604059D0 (sv)	1986-09-25
GR3003332T3 (en)	1993-02-17
FI874189L (sv)	1988-03-26
IL83994A (en)	1992-02-16
HK46194A (en)	1994-05-20
DE3774987D1 (de)	1992-01-16
KR950014460B1 (ko)	1995-11-28
ATE70066T1 (de)	1991-12-15
JPS6393795A (ja)	1988-04-25
ES2026576T3 (es)	1992-05-01
FI874189A0 (sv)	1987-09-24

Publication	Publication Date	Title
FI90345B (sv)	1993-10-15	Förfarande för kontroll av epimerdistributionen vid framställning av 16,17-acetaler av pregnanderivat
DE69717836T2 (de)	2003-09-18	Verfahren zur anreichung des verhältnisses der r-epimers von 16,17-acetal derivate von 21-acyloxy pregan-1,4-dien-11.beta.,16.alpha.,17.alpha.-triol-3,20-dionen
KR100809510B1 (ko)	2008-03-04	트랜스케탈화 반응에 의한 16,17-[(시클로헥실메틸렌)비스(옥시)]-11,21-디히드록시-프레그나-1,4-디엔-3,20-디온또는 이의 21-이소부티라트의 제조방법
EP2596007B1 (en)	2016-01-06	Process for the preparation of 17-desoxy-corticosteroids
EP0994119B1 (en)	2004-03-31	Stereoselective process for the preparation of the 22R epimer of budesonide
JPH02279697A (ja)	1990-11-15	新規ステロイド化合物およびそれを含む医薬組成物
DE10055820C1 (de)	2002-07-25	Verfahren zur Herstellung eines Glucocorticoids
US8049021B2 (en)	2011-11-01	Process for the preparation of fluorotetraene
HU199872B (en)	1990-03-28	Process for producing 16alpha,17alpha-alkilidenedioxy-11beta-hydroxypregno-1,4-diene-3,20-dione derivatives
AU2002229536B2 (en)	2007-04-19	Process for the production of 16,17-[(cyclohexylmethylen)bis(oxy)]-11,21-Dihydroxy-pregna-1,4-dien-3,20-dion or its21-isobutyrat by transketalisation
JPS6362516B2 (sv)	1988-12-02
US3996358A (en)	1976-12-07	21-Esters of steroidal-21-aldehyde hydrates and 21-aldehyde hemiacetals and methods of preparation
WO2005005454A1 (en)	2005-01-20	Steroid modified chacotrioses and solatrioses
US20030088090A1 (en)	2003-05-08	Stereoselective transacetalization of steroidal C-22 acetonide
HK1027579A (en)	2001-01-19	Stereoselective process for the preparation of the 22r epimer of budesonide
AU2002229536A1 (en)	2002-07-25	Process for the production of 16,17-[(cyclohexylmethylen)bis(oxy)]-11,21-Dihydroxy-pregna-1,4-dien-3,20-dion or its21-isobutyrat by transketalisation
HK1058043B (en)	2011-05-13	Process for the production of 16,17-[(cyclohexylmethylen)bis(oxy)]-11,21-dihydroxy-pregna-1,4-dien-3,20-dion or its 21-isobutyrat by transketalisation

Legal Events

Date	Code	Title	Description
1993-09-16	BB	Publication of examined application
2004-08-31	MM	Patent lapsed	Owner name: ASTRA PHARMACEUTICAL PRODUCTION AB