NO311242B1 - Anvendelse av 2-fenyl-3-aroylbenzotiofener for fremstilling av medikament for hemming av endometriose - Google Patents

Anvendelse av 2-fenyl-3-aroylbenzotiofener for fremstilling av medikament for hemming av endometriose Download PDF

Info

Publication number: NO311242B1
Authority: NO; Norway
Prior art keywords: compound; endometriosis; formula; endometrial; phenyl
Prior art date: 1993-10-15

Application number

NO19943879A

Other languages

English (en)

Norwegian (no)

Other versions

NO943879D0 (no

NO943879L (no

Inventor

Larry John Black

George Joseph Cullinan

Michael William Draper

Charles David Jones

David Edward Seyler

Original Assignee

Lilly Co Eli

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.)

1993-10-15

Filing date

1994-10-13

Publication date

2001-11-05

1994-10-13 Application filed by Lilly Co Eli filed Critical Lilly Co Eli

1994-10-13 Publication of NO943879D0 publication Critical patent/NO943879D0/no

1995-04-18 Publication of NO943879L publication Critical patent/NO943879L/no

2001-11-05 Publication of NO311242B1 publication Critical patent/NO311242B1/no

Links

201000009273 Endometriosis Diseases 0.000 title claims abstract description 15
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238000002360 preparation method Methods 0.000 title description 2
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150000003839 salts Chemical class 0.000 claims abstract description 17
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 5
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YQEMORVAKMFKLG-UHFFFAOYSA-N glycerine monostearate Natural products CCCCCCCCCCCCCCCCCC(=O)OC(CO)CO YQEMORVAKMFKLG-UHFFFAOYSA-N 0.000 description 1
SVUQHVRAGMNPLW-UHFFFAOYSA-N glycerol monostearate Natural products CCCCCCCCCCCCCCCCC(=O)OCC(O)CO SVUQHVRAGMNPLW-UHFFFAOYSA-N 0.000 description 1
239000003102 growth factor Substances 0.000 description 1
239000000122 growth hormone Substances 0.000 description 1
MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 1
238000010562 histological examination Methods 0.000 description 1
230000003054 hormonal effect Effects 0.000 description 1
229940088597 hormone Drugs 0.000 description 1
239000005556 hormone Substances 0.000 description 1
238000001794 hormone therapy Methods 0.000 description 1
239000003906 humectant Substances 0.000 description 1
229910000042 hydrogen bromide Inorganic materials 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
229910000043 hydrogen iodide Inorganic materials 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
TVZISJTYELEYPI-UHFFFAOYSA-N hypodiphosphoric acid Chemical compound OP(O)(=O)P(O)(O)=O TVZISJTYELEYPI-UHFFFAOYSA-N 0.000 description 1
230000006698 induction Effects 0.000 description 1
230000008595 infiltration Effects 0.000 description 1
238000001764 infiltration Methods 0.000 description 1
230000000977 initiatory effect Effects 0.000 description 1
SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 1
KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 1
TWBYWOBDOCUKOW-UHFFFAOYSA-M isonicotinate Chemical compound [O-]C(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-M 0.000 description 1
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
239000007788 liquid Substances 0.000 description 1
230000004807 localization Effects 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
210000002540 macrophage Anatomy 0.000 description 1
229940049920 malate Drugs 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
IWYDHOAUDWTVEP-UHFFFAOYSA-M mandelate Chemical compound [O-]C(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-M 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
230000001356 masculinizing effect Effects 0.000 description 1
125000005341 metaphosphate group Chemical group 0.000 description 1
IZYBEMGNIUSSAX-UHFFFAOYSA-N methyl benzenecarboperoxoate Chemical compound COOC(=O)C1=CC=CC=C1 IZYBEMGNIUSSAX-UHFFFAOYSA-N 0.000 description 1
229940095102 methyl benzoate Drugs 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
238000002156 mixing Methods 0.000 description 1
PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 1
235000001968 nicotinic acid Nutrition 0.000 description 1
239000011664 nicotinic acid Substances 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
WWZKQHOCKIZLMA-UHFFFAOYSA-M octanoate Chemical compound CCCCCCCC([O-])=O WWZKQHOCKIZLMA-UHFFFAOYSA-M 0.000 description 1
238000009806 oophorectomy Methods 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
KVNYFPKFSJIPBJ-UHFFFAOYSA-N ortho-diethylbenzene Natural products CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 1
239000012188 paraffin wax Substances 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
210000003200 peritoneal cavity Anatomy 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
DYUMLJSJISTVPV-UHFFFAOYSA-N phenyl propanoate Chemical compound CCC(=O)OC1=CC=CC=C1 DYUMLJSJISTVPV-UHFFFAOYSA-N 0.000 description 1
229940049953 phenylacetate Drugs 0.000 description 1
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
229950009215 phenylbutanoic acid Drugs 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
239000006187 pill Substances 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
230000009696 proliferative response Effects 0.000 description 1
UORVCLMRJXCDCP-UHFFFAOYSA-M propynoate Chemical compound [O-]C(=O)C#C UORVCLMRJXCDCP-UHFFFAOYSA-M 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
GZUITABIAKMVPG-UHFFFAOYSA-N raloxifene Chemical compound C1=CC(O)=CC=C1C1=C(C(=O)C=2C=CC(OCCN3CCCCC3)=CC=2)C2=CC=C(O)C=C2S1 GZUITABIAKMVPG-UHFFFAOYSA-N 0.000 description 1
229960004622 raloxifene Drugs 0.000 description 1
239000000376 reactant Substances 0.000 description 1
230000001850 reproductive effect Effects 0.000 description 1
229960001860 salicylate Drugs 0.000 description 1
229940116351 sebacate Drugs 0.000 description 1
CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 description 1
210000002966 serum Anatomy 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical class O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
108020003113 steroid hormone receptors Proteins 0.000 description 1
102000005969 steroid hormone receptors Human genes 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
TYFQFVWCELRYAO-UHFFFAOYSA-L suberate(2-) Chemical compound [O-]C(=O)CCCCCCC([O-])=O TYFQFVWCELRYAO-UHFFFAOYSA-L 0.000 description 1
239000000126 substance Substances 0.000 description 1
229940086735 succinate Drugs 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
230000001629 suppression Effects 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000007916 tablet composition Substances 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
238000010998 test method Methods 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
WBYWAXJHAXSJNI-VOTSOKGWSA-M trans-cinnamate Chemical compound [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
239000001993 wax Substances 0.000 description 1
230000003442 weekly effect Effects 0.000 description 1
229940071104 xylenesulfonate Drugs 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
- A61K31/33—Heterocyclic compounds
- A61K31/38—Heterocyclic compounds having sulfur as a ring hetero atom
- A61K31/381—Heterocyclic compounds having sulfur as a ring hetero atom having five-membered rings
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/38—Heterocyclic compounds having sulfur as a ring hetero atom
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/4025—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil not condensed and containing further heterocyclic rings, e.g. cromakalim
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/4535—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a heterocyclic ring having sulfur as a ring hetero atom, e.g. pizotifen
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
- 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
- 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
- A61P15/02—Drugs for genital or sexual disorders; Contraceptives for disorders of the vagina
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings

Landscapes

Health & Medical Sciences (AREA)
Public Health (AREA)
Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Medicinal Chemistry (AREA)
Veterinary Medicine (AREA)
General Health & Medical Sciences (AREA)
Epidemiology (AREA)
Bioinformatics & Cheminformatics (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Reproductive Health (AREA)
Endocrinology (AREA)
Urology & Nephrology (AREA)
Gynecology & Obstetrics (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Steroid Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Cable Transmission Systems, Equalization Of Radio And Reduction Of Echo (AREA)

NO19943879A 1993-10-15 1994-10-13 Anvendelse av 2-fenyl-3-aroylbenzotiofener for fremstilling av medikament for hemming av endometriose NO311242B1 (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US08/138,643 US5461065A (en)	1993-10-15	1993-10-15	Methods for inhibiting endometriosis

Publications (3)

Publication Number	Publication Date
NO943879D0 NO943879D0 (no)	1994-10-13
NO943879L NO943879L (no)	1995-04-18
NO311242B1 true NO311242B1 (no)	2001-11-05

Family

ID=22482966

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO19943879A NO311242B1 (no)	1993-10-15	1994-10-13	Anvendelse av 2-fenyl-3-aroylbenzotiofener for fremstilling av medikament for hemming av endometriose

Country Status (25)

Country	Link
US (2)	US5461065A (uk)
EP (1)	EP0652005B1 (uk)
JP (1)	JPH07188014A (uk)
KR (1)	KR950010893A (uk)
CN (1)	CN1049335C (uk)
AT (1)	ATE203404T1 (uk)
AU (1)	AU677700B2 (uk)
CA (1)	CA2118092A1 (uk)
CZ (1)	CZ287246B6 (uk)
DE (1)	DE69427800T2 (uk)
DK (1)	DK0652005T3 (uk)
ES (1)	ES2157957T3 (uk)
GR (1)	GR3036971T3 (uk)
HU (1)	HUT71235A (uk)
IL (1)	IL111284A (uk)
NO (1)	NO311242B1 (uk)
NZ (1)	NZ264677A (uk)
PH (1)	PH31261A (uk)
PT (1)	PT652005E (uk)
RU (1)	RU2157203C2 (uk)
SG (1)	SG43319A1 (uk)
SI (1)	SI0652005T1 (uk)
TW (1)	TW296382B (uk)
UA (1)	UA26930C2 (uk)
ZA (1)	ZA948029B (uk)

Families Citing this family (29)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5811447A (en)	1993-01-28	1998-09-22	Neorx Corporation	Therapeutic inhibitor of vascular smooth muscle cells
US6515009B1 (en)	1991-09-27	2003-02-04	Neorx Corporation	Therapeutic inhibitor of vascular smooth muscle cells
USRE39049E1 (en)	1992-07-28	2006-03-28	Eli Lilly And Company	Methods for inhibiting bone loss
TW366342B (en) *	1992-07-28	1999-08-11	Lilly Co Eli	The use of 2-phenyl-3-aroylbenzothiophenes in inhibiting bone loss
USRE38968E1 (en)	1992-07-28	2006-02-07	Eli Lilly And Company	Methods for inhibiting bone loss using 6-hydroxy-2-(4-hydroxyphenyl)-benzo[b]thien-3-yl-4-[2-(piperidin-1-yl) ethoxyphenylimethanone hydrochloride
US6491938B2 (en)	1993-05-13	2002-12-10	Neorx Corporation	Therapeutic inhibitor of vascular smooth muscle cells
US5595722A (en)	1993-01-28	1997-01-21	Neorx Corporation	Method for identifying an agent which increases TGF-beta levels
CA2162586C (en)	1993-05-13	2006-01-03	David J. Grainger	Prevention and treatment of pathologies associated with abnormally proliferative smooth muscle cells
US5457116A (en) *	1993-10-15	1995-10-10	Eli Lilly And Company	Methods of inhibiting uterine fibrosis
US5478847A (en)	1994-03-02	1995-12-26	Eli Lilly And Company	Methods of use for inhibiting bone loss and lowering serum cholesterol
MX9701359A (es) *	1994-08-22	1997-05-31	Lilly Co Eli	Metodos para la inhibicion de la hiperplasia endometrial primaria.
US5843964A (en) *	1994-09-22	1998-12-01	Eli Lilly And Company	Methods of inhibiting endometrial mitoses
US5554600A (en) *	1995-01-20	1996-09-10	Eli Lilly And Company	Methods for inhibiting endometriosis
EP0747380B1 (en) *	1995-06-07	1998-09-30	Eli Lilly And Company	Compounds and compositions with nitrogen-containing non-basic side chains
KR970002795A (ko)	1995-10-30	1997-01-28	모리 하루오	네비게이션(navigation)장치
IL120266A (en) *	1996-02-28	2005-05-17	Pfizer	Use of estrogen antagonists and estrogen agonists in the preparation of medicaments for inhibiting pathological conditions
TW442286B (en) *	1996-02-28	2001-06-23	Pfizer	New therapeutic uses of estrogen agonists
CA2214072C (en) *	1996-08-29	2006-11-14	Eli Lilly And Company	Benzo [b] thiophene compounds, intermediates, processes, compositions, and methods
US6117911A (en) *	1997-04-11	2000-09-12	Neorx Corporation	Compounds and therapies for the prevention of vascular and non-vascular pathologies
US5942539A (en) *	1997-10-03	1999-08-24	Wake Forest University	Methods of treating or preventing endometriosis with phytoestrogens
US6187777B1 (en)	1998-02-06	2001-02-13	Amgen Inc.	Compounds and methods which modulate feeding behavior and related diseases
KR20010080254A (ko) *	1998-11-26	2001-08-22	야마구찌 다까시	주기 투여용 의약조성물
HUP0200871A3 (en)	1999-05-04	2004-04-28	Strakan Int Ltd	Androgen glycosides and androgenic activity thereof
WO2002056903A2 (en) *	2001-01-17	2002-07-25	Praecis Pharmaceuticals Inc.	Methods for treating hormone associated conditions using a combination of lhrh antagonists and specific estrogen receptor modulators
ES2236536T3 (es) *	2001-05-22	2005-07-16	Eli Lilly And Company	Derivados tetrahidroquinolino para la inhibicion de enfermedades asociadas con la privacion de estrogenos o con una respuesta fisiologica aberrante a estrogenos endogenos.
US7056931B2 (en) *	2001-05-22	2006-06-06	Eli Lilly And Company	2-substituted 1,2,3,4-tetrahydroquinolines and derivatives thereof, compositions and methods
US7488734B2 (en) *	2002-06-25	2009-02-10	Wyeth	Methods of treating hormone-related conditions using thio-oxindole derivatives
US20060106010A1 (en) *	2003-05-27	2006-05-18	Black Larry J	Methods for inhibiting bone loss
US11576891B2 (en)	2010-06-16	2023-02-14	Endorecherche, Inc.	Methods of treating or preventing estrogen-related diseases

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4133814A (en) *	1975-10-28	1979-01-09	Eli Lilly And Company	2-Phenyl-3-aroylbenzothiophenes useful as antifertility agents
US4418068A (en) *	1981-04-03	1983-11-29	Eli Lilly And Company	Antiestrogenic and antiandrugenic benzothiophenes
US4380635A (en) *	1981-04-03	1983-04-19	Eli Lilly And Company	Synthesis of acylated benzothiophenes
US5075321A (en) *	1987-03-24	1991-12-24	University Of Pennsylvania	Methods of treating diseases characterized by interactions of IgG-containing immune complexes with macrophage Fc receptors using antiestrogenic benzothiophenes
US5395842A (en) *	1988-10-31	1995-03-07	Endorecherche Inc.	Anti-estrogenic compounds and compositions
SE500453C2 (sv) *	1991-10-07	1994-06-27	Karobio Ab	Ett in vitro förfarande för utvärdering av en substans effekter
JP3157882B2 (ja) *	1991-11-15	2001-04-16	帝国臓器製薬株式会社	新規なベンゾチオフエン誘導体

1993
- 1993-10-15 US US08/138,643 patent/US5461065A/en not_active Expired - Lifetime
1994
- 1994-10-12 UA UA94105917A patent/UA26930C2/uk unknown
- 1994-10-13 CN CN94117125A patent/CN1049335C/zh not_active Expired - Fee Related
- 1994-10-13 ZA ZA948029A patent/ZA948029B/xx unknown
- 1994-10-13 EP EP94307528A patent/EP0652005B1/en not_active Expired - Lifetime
- 1994-10-13 RU RU94036772/14A patent/RU2157203C2/ru active
- 1994-10-13 DK DK94307528T patent/DK0652005T3/da active
- 1994-10-13 JP JP6247764A patent/JPH07188014A/ja active Pending
- 1994-10-13 PT PT94307528T patent/PT652005E/pt unknown
- 1994-10-13 ES ES94307528T patent/ES2157957T3/es not_active Expired - Lifetime
- 1994-10-13 CZ CZ19942537A patent/CZ287246B6/cs not_active IP Right Cessation
- 1994-10-13 TW TW083109467A patent/TW296382B/zh active
- 1994-10-13 DE DE69427800T patent/DE69427800T2/de not_active Expired - Fee Related
- 1994-10-13 NZ NZ264677A patent/NZ264677A/en unknown
- 1994-10-13 SI SI9430388T patent/SI0652005T1/xx unknown
- 1994-10-13 SG SG1996008246A patent/SG43319A1/en unknown
- 1994-10-13 AU AU75787/94A patent/AU677700B2/en not_active Ceased
- 1994-10-13 IL IL11128494A patent/IL111284A/xx not_active IP Right Cessation
- 1994-10-13 HU HU9402959A patent/HUT71235A/hu unknown
- 1994-10-13 AT AT94307528T patent/ATE203404T1/de not_active IP Right Cessation
- 1994-10-13 PH PH49186A patent/PH31261A/en unknown
- 1994-10-13 KR KR1019940026164A patent/KR950010893A/ko not_active Application Discontinuation
- 1994-10-13 CA CA002118092A patent/CA2118092A1/en not_active Abandoned
- 1994-10-13 NO NO19943879A patent/NO311242B1/no not_active IP Right Cessation
1995
- 1995-04-14 US US08/422,387 patent/US5693656A/en not_active Expired - Fee Related
2001
- 2001-10-22 GR GR20010401841T patent/GR3036971T3/el not_active IP Right Cessation

Also Published As

Publication number	Publication date
HU9402959D0 (en)	1995-02-28
ZA948029B (en)	1996-04-15
CZ253794A3 (en)	1995-05-17
HUT71235A (en)	1995-11-28
US5461065A (en)	1995-10-24
PT652005E (pt)	2001-11-30
JPH07188014A (ja)	1995-07-25
AU677700B2 (en)	1997-05-01
AU7578794A (en)	1995-05-04
CN1049335C (zh)	2000-02-16
EP0652005B1 (en)	2001-07-25
NZ264677A (en)	1997-07-27
NO943879D0 (no)	1994-10-13
CZ287246B6 (en)	2000-10-11
NO943879L (no)	1995-04-18
IL111284A0 (en)	1994-12-29
GR3036971T3 (en)	2002-01-31
DK0652005T3 (da)	2001-09-24
CA2118092A1 (en)	1995-04-16
EP0652005A1 (en)	1995-05-10
ES2157957T3 (es)	2001-09-01
US5693656A (en)	1997-12-02
RU2157203C2 (ru)	2000-10-10
SG43319A1 (en)	1997-10-17
DE69427800T2 (de)	2001-12-06
ATE203404T1 (de)	2001-08-15
IL111284A (en)	2000-02-29
RU94036772A (ru)	1996-08-27
CN1107043A (zh)	1995-08-23
TW296382B (uk)	1997-01-21
UA26930C2 (uk)	1999-12-29
SI0652005T1 (en)	2001-12-31
DE69427800D1 (de)	2001-08-30
KR950010893A (ko)	1995-05-15
PH31261A (en)	1998-06-18

Publication	Publication Date	Title
NO311242B1 (no)	2001-11-05	Anvendelse av 2-fenyl-3-aroylbenzotiofener for fremstilling av medikament for hemming av endometriose
US5455275A (en)	1995-10-03	Methods for inhibiting endometriosis and uterine fibroid disease with 1,1,2-triphenylbut-1-ene derivatives
US5457116A (en)	1995-10-10	Methods of inhibiting uterine fibrosis
US5446053A (en)	1995-08-29	Methods of inhibiting dysfunctional uterine bleeding
US5663184A (en)	1997-09-02	Methods of inhibiting CNS problems in post-menopausal women
HUT71477A (en)	1995-11-28	Pharmaceutical compositions for increasing libido in post-menopausal women containing 2-phenyl-3-aroil-benzothiophene derivatives and process for their preparation
US5451589A (en)	1995-09-19	Methods of inhibiting ovarian dysgenesis, delayed puberty, or sexual infantilism
US5502074A (en)	1996-03-26	Benzothiophenes for bone healing and fracture repair
US5554600A (en)	1996-09-10	Methods for inhibiting endometriosis
AU706953B2 (en)	1999-07-01	Methods of inhibiting primary endometrial hyperplasia
KR19980701329A (ko)	1998-05-15	성장 호르몬 효과의 억제 방법(Methods of Inhibiting Growth Hormone Effects)

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2003-06-02	MM1K	Lapsed by not paying the annual fees	Free format text: LAPSED IN APRIL 2003