TW201026718A - Use of 17β-cyano-19-androst-4-ene derivatives for preparing a medicament in depot form for parenteral administration and depot medicaments comprising 17β-cyano-19-androst-4-ene derivatives for parenteral administration - Google Patents

Use of 17β-cyano-19-androst-4-ene derivatives for preparing a medicament in depot form for parenteral administration and depot medicaments comprising 17β-cyano-19-androst-4-ene derivatives for parenteral administration Download PDF

Info

Publication number: TW201026718A
Authority: TW; Taiwan
Prior art keywords: group; hydrogen; cyano; methyl; ene
Prior art date: 2008-12-12

Application number

TW098142628A

Other languages

English (en)

Chinese (zh)

Inventor

Norbert Schmees

Katja Prelle

Joachim Kuhnke

Original Assignee

Bayer Schering Pharma Ag

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.)

2008-12-12

Filing date

2009-12-11

Publication date

2010-07-16

2009-12-11 Application filed by Bayer Schering Pharma Ag filed Critical Bayer Schering Pharma Ag

2010-07-16 Publication of TW201026718A publication Critical patent/TW201026718A/zh

Links

239000003814 drug Substances 0.000 title claims abstract description 20
238000007911 parenteral administration Methods 0.000 title 2
150000001875 compounds Chemical class 0.000 claims abstract description 62
239000001257 hydrogen Substances 0.000 claims abstract description 56
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 56
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims abstract description 43
-1 hydroxymethylene Chemical group 0.000 claims abstract description 39
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 38
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 35
239000000126 substance Substances 0.000 claims abstract description 24
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 23
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims abstract description 18
150000003839 salts Chemical class 0.000 claims abstract description 8
239000012453 solvate Substances 0.000 claims abstract description 8
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims abstract description 6
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims abstract description 6
150000004677 hydrates Chemical class 0.000 claims abstract description 5
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims abstract description 4
229910052736 halogen Chemical group 0.000 claims abstract description 3
150000002367 halogens Chemical group 0.000 claims abstract description 3
238000002360 preparation method Methods 0.000 claims description 54
229940011871 estrogen Drugs 0.000 claims description 24
239000000262 estrogen Substances 0.000 claims description 24
230000035935 pregnancy Effects 0.000 claims description 18
230000000694 effects Effects 0.000 claims description 16
125000000217 alkyl group Chemical group 0.000 claims description 13
229940079593 drug Drugs 0.000 claims description 13
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
239000007789 gas Chemical group 0.000 claims description 10
125000005577 anthracene group Chemical group 0.000 claims description 5
125000003342 alkenyl group Chemical group 0.000 claims description 4
125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 4
239000002395 mineralocorticoid Substances 0.000 claims description 4
125000003396 thiol group Chemical group [H]S* 0.000 claims description 4
VOXZDWNPVJITMN-ZBRFXRBCSA-N 17β-estradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 VOXZDWNPVJITMN-ZBRFXRBCSA-N 0.000 claims description 3
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 3
150000001336 alkenes Chemical class 0.000 claims description 3
229960005309 estradiol Drugs 0.000 claims description 3
229930182833 estradiol Natural products 0.000 claims description 3
229940088597 hormone Drugs 0.000 claims description 3
239000005556 hormone Substances 0.000 claims description 3
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 3
229910052707 ruthenium Inorganic materials 0.000 claims description 3
125000001424 substituent group Chemical group 0.000 claims description 3
210000001215 vagina Anatomy 0.000 claims description 3
150000002009 diols Chemical class 0.000 claims description 2
MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims 2
VUUWICXRDSPFFL-WAJSLEGFSA-N C(CC(O)(C(=O)O)CC(=O)O)(=O)O.[C@@H]12CCC(O)[C@@]1(C)CC[C@@H]1C3=C(CC[C@@H]21)C=C(O)C=C3 Chemical compound C(CC(O)(C(=O)O)CC(=O)O)(=O)O.[C@@H]12CCC(O)[C@@]1(C)CC[C@@H]1C3=C(CC[C@@H]21)C=C(O)C=C3 VUUWICXRDSPFFL-WAJSLEGFSA-N 0.000 claims 1
210000003719 b-lymphocyte Anatomy 0.000 claims 1
QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 claims 1
239000000463 material Substances 0.000 claims 1
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125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
230000015572 biosynthetic process Effects 0.000 abstract description 10
239000006213 vaginal ring Substances 0.000 abstract description 5
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125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 3
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238000000034 method Methods 0.000 description 53
101150041968 CDC13 gene Proteins 0.000 description 52
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238000005481 NMR spectroscopy Methods 0.000 description 48
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235000019439 ethyl acetate Nutrition 0.000 description 34
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238000006243 chemical reaction Methods 0.000 description 26
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238000005160 1H NMR spectroscopy Methods 0.000 description 14
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
150000002576 ketones Chemical class 0.000 description 14
239000002585 base Substances 0.000 description 13
238000004587 chromatography analysis Methods 0.000 description 13
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
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YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
238000003818 flash chromatography Methods 0.000 description 12
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 11
125000004093 cyano group Chemical group *C#N 0.000 description 11
150000001993 dienes Chemical class 0.000 description 11
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 11
229910021653 sulphate ion Inorganic materials 0.000 description 11
239000002904 solvent Substances 0.000 description 10
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
239000000047 product Substances 0.000 description 9
MUCRYNWJQNHDJH-OADIDDRXSA-N Ursonic acid Chemical compound C1CC(=O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C(O)=O)CC[C@@H](C)[C@H](C)[C@H]5C4=CC[C@@H]3[C@]21C MUCRYNWJQNHDJH-OADIDDRXSA-N 0.000 description 8
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CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical class [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 7
239000013543 active substance Substances 0.000 description 7
239000003433 contraceptive agent Substances 0.000 description 7
239000012043 crude product Substances 0.000 description 7
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229960003387 progesterone Drugs 0.000 description 7
229920006395 saturated elastomer Polymers 0.000 description 7
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
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239000007858 starting material Substances 0.000 description 6
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AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 4
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238000006596 Alder-ene reaction Methods 0.000 description 3
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229910052794 bromium Inorganic materials 0.000 description 3
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238000001816 cooling Methods 0.000 description 3
229910052802 copper Inorganic materials 0.000 description 3
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UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
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125000000524 functional group Chemical group 0.000 description 3
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RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
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WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
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PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
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125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
229960003604 testosterone Drugs 0.000 description 1
FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 1
MCOWGUNDBBHKAM-UHFFFAOYSA-N thiohypoiodous acid Chemical compound IS MCOWGUNDBBHKAM-UHFFFAOYSA-N 0.000 description 1
CFOAUYCPAUGDFF-UHFFFAOYSA-N tosmic Chemical compound CC1=CC=C(S(=O)(=O)C[N+]#[C-])C=C1 CFOAUYCPAUGDFF-UHFFFAOYSA-N 0.000 description 1
238000009901 transfer hydrogenation reaction Methods 0.000 description 1
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JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
NRZWQKGABZFFKE-UHFFFAOYSA-N trimethylsulfonium Chemical compound C[S+](C)C NRZWQKGABZFFKE-UHFFFAOYSA-N 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
229960000281 trometamol Drugs 0.000 description 1
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238000001291 vacuum drying Methods 0.000 description 1
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239000000052 vinegar Substances 0.000 description 1
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239000011995 wilkinson's catalyst Substances 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/12—Drugs for genital or sexual disorders; Contraceptives for climacteric disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/18—Feminine contraceptives

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Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Endocrinology (AREA)
Reproductive Health (AREA)
Organic Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Gynecology & Obstetrics (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Steroid Compounds (AREA)
Medicinal Preparation (AREA)
Orthopedics, Nursing, And Contraception (AREA)

TW098142628A 2008-12-12 2009-12-11 Use of 17β-cyano-19-androst-4-ene derivatives for preparing a medicament in depot form for parenteral administration and depot medicaments comprising 17β-cyano-19-androst-4-ene derivatives for parenteral administration TW201026718A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE102008062445		2008-12-12
DE102008063791		2008-12-17

Publications (1)

Publication Number	Publication Date
TW201026718A true TW201026718A (en)	2010-07-16

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ID=41570906

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
TW098142628A TW201026718A (en)	2008-12-12	2009-12-11	Use of 17β-cyano-19-androst-4-ene derivatives for preparing a medicament in depot form for parenteral administration and depot medicaments comprising 17β-cyano-19-androst-4-ene derivatives for parenteral administration

Country Status (3)

Country	Link
AR (1)	AR074730A1 (de)
TW (1)	TW201026718A (de)
WO (1)	WO2010066349A1 (de)

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3705179A (en) *	1971-03-15	1972-12-05	American Home Prod	Antiandrogenic steroids
FR2139708B1 (de) *	1971-06-01	1974-08-23	Roussel Uclaf
US5182381A (en) *	1982-03-01	1993-01-26	Roussel Ulcaf	Intermediates for 3-keto-19-nor-Δ4,9 -steroids
DE19651000A1 (de) *	1996-12-01	1998-06-04	Schering Ag	Oxyiminopregnancarbolactone
DE102004063864A1 (de) *	2004-12-30	2006-07-13	Schering Ag	18-Methyl-19-nor-17-pregn-4-en21,17-carbolactone, sowie diese enthaltende pharmazeutische Präparate
DE102007027635A1 (de) *	2007-06-12	2008-12-18	Bayer Schering Pharma Aktiengesellschaft	17ß-Cyano-19-androst-4-en-Derivat, dessen Verwendung und das Derivat enthaltende Arzneimittel

2009
- 2009-11-28 WO PCT/EP2009/008480 patent/WO2010066349A1/de not_active Ceased
- 2009-12-11 TW TW098142628A patent/TW201026718A/zh unknown
- 2009-12-14 AR ARP090104844A patent/AR074730A1/es unknown

Also Published As

Publication number	Publication date
AR074730A1 (es)	2011-02-09
WO2010066349A1 (de)	2010-06-17

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