CA2099017A1 - D-homo-(16-en)-11.beta.-aryl-4-estrenes, methode de preparation et utilisation comme medicaments - Google Patents

D-homo-(16-en)-11.beta.-aryl-4-estrenes, methode de preparation et utilisation comme medicaments

Info

Publication number: CA2099017A1
Authority: CA; Canada
Prior art keywords: alpha; beta; hydroxy; group; homoestra
Prior art date: 1990-01-24
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.): Abandoned

Application number

CA 2099017

Other languages

English (en)

Inventor

Wolfgang Schwede

Eckhard Ottow

Arwed Cleve

Walter Elger

Krzysztof Chwalisz

Martin Schneider

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.)

Bayer Pharma AG

Original Assignee

Individual

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.)

1990-01-24

Filing date

1991-12-21

Publication date

1992-06-23

1991-12-21 Application filed by Individual filed Critical Individual

1992-06-23 Publication of CA2099017A1 publication Critical patent/CA2099017A1/fr

Status Abandoned legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 18
230000008569 process Effects 0.000 title claims abstract description 9
239000003814 drug Substances 0.000 title abstract 2
-1 hydroxyimino Chemical group 0.000 claims abstract description 73
150000001875 compounds Chemical class 0.000 claims abstract description 69
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 33
239000000460 chlorine Substances 0.000 claims abstract description 15
239000002253 acid Substances 0.000 claims abstract description 14
229910052801 chlorine Inorganic materials 0.000 claims abstract description 13
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 13
229910052731 fluorine Inorganic materials 0.000 claims abstract description 12
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 12
150000003839 salts Chemical class 0.000 claims abstract description 11
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 9
239000011737 fluorine Substances 0.000 claims abstract description 9
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 6
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims abstract description 6
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 6
125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 5
239000013067 intermediate product Substances 0.000 claims abstract description 4
125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims abstract description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 32
229920006395 saturated elastomer Polymers 0.000 claims description 18
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 12
229910052794 bromium Inorganic materials 0.000 claims description 10
238000004519 manufacturing process Methods 0.000 claims description 10
230000015572 biosynthetic process Effects 0.000 claims description 9
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229910052740 iodine Inorganic materials 0.000 claims description 9
150000003254 radicals Chemical class 0.000 claims description 9
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ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 7
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239000001257 hydrogen Substances 0.000 claims description 7
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125000002252 acyl group Chemical group 0.000 claims description 6
125000003277 amino group Chemical group 0.000 claims description 6
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230000000694 effects Effects 0.000 claims description 6
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239000008177 pharmaceutical agent Substances 0.000 claims description 6
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ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 5
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IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
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125000004183 alkoxy alkyl group Chemical group 0.000 claims description 3
239000003795 chemical substances by application Substances 0.000 claims description 3
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239000000825 pharmaceutical preparation Substances 0.000 claims description 3
125000004665 trialkylsilyl group Chemical group 0.000 claims description 3
125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 2
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235000010290 biphenyl Nutrition 0.000 claims description 2
125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 2
125000000468 ketone group Chemical group 0.000 claims description 2
229910052717 sulfur Inorganic materials 0.000 claims description 2
125000004434 sulfur atom Chemical group 0.000 claims description 2
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 claims 2
NKCCODPFBDGPRJ-UHFFFAOYSA-N nitridocarbon(1+) Chemical compound N#[C+] NKCCODPFBDGPRJ-UHFFFAOYSA-N 0.000 claims 2
125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 1
230000018044 dehydration Effects 0.000 claims 1
238000006297 dehydration reaction Methods 0.000 claims 1
239000003937 drug carrier Substances 0.000 claims 1
230000007717 exclusion Effects 0.000 claims 1
150000002431 hydrogen Chemical class 0.000 claims 1
125000004043 oxo group Chemical group O=* 0.000 claims 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
239000001294 propane Substances 0.000 claims 1
125000000101 thioether group Chemical group 0.000 claims 1
150000007513 acids Chemical class 0.000 abstract description 7
239000000583 progesterone congener Substances 0.000 abstract description 4
239000008194 pharmaceutical composition Substances 0.000 abstract description 2
230000002860 competitive effect Effects 0.000 abstract 1
239000000044 progesterone antagonist Substances 0.000 abstract 1
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239000000243 solution Substances 0.000 description 72
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235000019439 ethyl acetate Nutrition 0.000 description 44
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239000000203 mixture Substances 0.000 description 37
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238000005160 1H NMR spectroscopy Methods 0.000 description 24
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229910052938 sodium sulfate Inorganic materials 0.000 description 22
235000011152 sodium sulphate Nutrition 0.000 description 22
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
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YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
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125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 16
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ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
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229910052744 lithium Inorganic materials 0.000 description 10
KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 10
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UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
238000003786 synthesis reaction Methods 0.000 description 7
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NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 6
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125000003118 aryl group Chemical group 0.000 description 5
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GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 4
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239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
FDRCDNZGSXJAFP-UHFFFAOYSA-M sodium chloroacetate Chemical compound [Na+].[O-]C(=O)CCl FDRCDNZGSXJAFP-UHFFFAOYSA-M 0.000 description 1
RMBAVIFYHOYIFM-UHFFFAOYSA-M sodium methanethiolate Chemical compound [Na+].[S-]C RMBAVIFYHOYIFM-UHFFFAOYSA-M 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical class [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
QJDUDPQVDAASMV-UHFFFAOYSA-M sodium;ethanethiolate Chemical compound [Na+].CC[S-] QJDUDPQVDAASMV-UHFFFAOYSA-M 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
229940037128 systemic glucocorticoids Drugs 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
150000003505 terpenes Chemical class 0.000 description 1
BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
150000003606 tin compounds Chemical class 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
150000003623 transition metal compounds Chemical class 0.000 description 1
DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 description 1
125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 description 1
210000004291 uterus Anatomy 0.000 description 1
239000000341 volatile oil Substances 0.000 description 1
238000009736 wetting Methods 0.000 description 1

Classifications

- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01S—DEVICES USING THE PROCESS OF LIGHT AMPLIFICATION BY STIMULATED EMISSION OF RADIATION [LASER] TO AMPLIFY OR GENERATE LIGHT; DEVICES USING STIMULATED EMISSION OF ELECTROMAGNETIC RADIATION IN WAVE RANGES OTHER THAN OPTICAL
- H01S3/00—Lasers, i.e. devices using stimulated emission of electromagnetic radiation in the infrared, visible or ultraviolet wave range
- H01S3/02—Constructional details
- H01S3/03—Constructional details of gas laser discharge tubes
- H01S3/032—Constructional details of gas laser discharge tubes for confinement of the discharge, e.g. by special features of the discharge constricting tube
- H01S3/0323—Constructional details of gas laser discharge tubes for confinement of the discharge, e.g. by special features of the discharge constricting tube by special features of the discharge constricting tube, e.g. capillary

Landscapes

Physics & Mathematics (AREA)
Electromagnetism (AREA)
Engineering & Computer Science (AREA)
Plasma & Fusion (AREA)
Optics & Photonics (AREA)
Lasers (AREA)
Steroid Compounds (AREA)

CA 2099017 1990-01-24 1991-12-21 D-homo-(16-en)-11.beta.-aryl-4-estrenes, methode de preparation et utilisation comme medicaments Abandoned CA2099017A1 (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE19904002005 DE4002005C2 (de)	1990-01-24	1990-01-24	Edelgasionenlaser
DEP4002005.1		1990-12-22

Publications (1)

Publication Number	Publication Date
CA2099017A1 true CA2099017A1 (fr)	1992-06-23

Family

ID=6398676

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA 2099017 Abandoned CA2099017A1 (fr)	1990-01-24	1991-12-21	D-homo-(16-en)-11.beta.-aryl-4-estrenes, methode de preparation et utilisation comme medicaments

Country Status (2)

Country	Link
CA (1)	CA2099017A1 (fr)
DE (1)	DE4002005C2 (fr)

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0177729B1 (fr) *	1984-09-26	1990-10-31	Siemens Aktiengesellschaft	Fonctionnement et utilisation d'un laser à gaz nobles ionisés

1990
- 1990-01-24 DE DE19904002005 patent/DE4002005C2/de not_active Expired - Fee Related
1991
- 1991-12-21 CA CA 2099017 patent/CA2099017A1/fr not_active Abandoned

Also Published As

Publication number	Publication date
DE4002005C2 (de)	1994-09-08
DE4002005A1 (de)	1991-07-25

Publication	Publication Date	Title
US5728689A (en)	1998-03-17	11β-aryl-4-estrenes, process for their production as well as their use as pharmaceutical agents
US4870069A (en)	1989-09-26	11β-alkynyl-estrenes and -estradienes, their production and pharmaceutical preparations containing them
IE872017L (en)	1988-01-25	11ß-(4-ISOPROPENYLPHENYL)OESTRA-4,9-DIENES
IE70664B1 (en)	1996-12-11	13-alkyl-11Beta-phenylgonanes
CA1339924C (fr)	1998-06-23	Sterioides 11beta-penyl-14betha
US5093507A (en)	1992-03-03	10β,11β-bridged steroids
EP0567469B1 (fr)	1997-08-27	14beta-H-, 14- ET 15-EN-11beta-ARYL-4-ESTRENES
US5232915A (en)	1993-08-03	9α-hydroxy-19,11β-bridged steroids, their production and pharmaceutical preparations containing these steroids
JP3202229B2 (ja)	2001-08-27	８−エン−１９，１１β−架橋したステロイド、その製造方法および該ステロイドを含有する製薬的製剤
US5519027A (en)	1996-05-21	D-homo-(16-ene)-11β-aryl-4-estrenes, process for their production as well as their use as pharmaceutical agents
JP3181589B2 (ja)	2001-07-03	６、７−変性１１β−アリール−４−エステレン
US5446178A (en)	1995-08-29	Process for preparing 19,11β-bridged steroids
EP0532562A1 (fr)	1993-03-24	PROCEDE DE PRODUCTION DE 10-g(b)-H-STEROIDS.
CA2099017A1 (fr)	1992-06-23	D-homo-(16-en)-11.beta.-aryl-4-estrenes, methode de preparation et utilisation comme medicaments
FI110688B (fi)	2003-03-14	11 beta-aryyli-4-estreenejä ja menetelmä niiden valmistamiseksi
PT100055B (pt)	1999-08-31	D-homo-(16-eno)-11b-aril-4-estrenos, processo para a sua preparacao bem como a sua utilizacao como medicamentos

Legal Events

Date	Code	Title	Description
1998-12-21	FZDE	Dead