NO309361B1 - Anvendelse av 3,4-diarylkromaner til fremstilling av farmasöytiske preparater - Google Patents
Anvendelse av 3,4-diarylkromaner til fremstilling av farmasöytiske preparater Download PDFInfo
- Publication number
- NO309361B1 NO309361B1 NO953542A NO953542A NO309361B1 NO 309361 B1 NO309361 B1 NO 309361B1 NO 953542 A NO953542 A NO 953542A NO 953542 A NO953542 A NO 953542A NO 309361 B1 NO309361 B1 NO 309361B1
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- Prior art keywords
- bone
- use according
- bone loss
- acid
- preparation
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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
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only 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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
Landscapes
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Physical Education & Sports Medicine (AREA)
- Rheumatology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Prostheses (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Saccharide Compounds (AREA)
- Pyrane Compounds (AREA)
- Medicinal Preparation (AREA)
- Pens And Brushes (AREA)
- Confectionery (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US08/029,729 US5280040A (en) | 1993-03-11 | 1993-03-11 | Methods for reducing bone loss using centchroman derivatives |
PCT/US1994/000633 WO1994020098A1 (en) | 1993-03-11 | 1994-01-13 | Methods for inhibiting bone loss with 3,4-diarylchroman |
Publications (3)
Publication Number | Publication Date |
---|---|
NO953542D0 NO953542D0 (no) | 1995-09-08 |
NO953542L NO953542L (no) | 1995-09-08 |
NO309361B1 true NO309361B1 (no) | 2001-01-22 |
Family
ID=21850559
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO953542A NO309361B1 (no) | 1993-03-11 | 1995-09-08 | Anvendelse av 3,4-diarylkromaner til fremstilling av farmasöytiske preparater |
Country Status (19)
Country | Link |
---|---|
US (2) | US5280040A (hu) |
EP (1) | EP0688214B1 (hu) |
JP (1) | JP2834581B2 (hu) |
KR (1) | KR100263009B1 (hu) |
AT (1) | ATE178488T1 (hu) |
AU (2) | AU674394B2 (hu) |
BR (1) | BR9405843A (hu) |
CA (1) | CA2157879C (hu) |
CZ (1) | CZ287603B6 (hu) |
DE (1) | DE69417733T2 (hu) |
DK (1) | DK0688214T3 (hu) |
ES (1) | ES2131678T3 (hu) |
GR (1) | GR3030128T3 (hu) |
HU (1) | HUT74575A (hu) |
NO (1) | NO309361B1 (hu) |
NZ (1) | NZ262569A (hu) |
RU (1) | RU2166940C2 (hu) |
SG (1) | SG65584A1 (hu) |
WO (1) | WO1994020098A1 (hu) |
Families Citing this family (79)
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 |
US6491938B2 (en) | 1993-05-13 | 2002-12-10 | Neorx Corporation | Therapeutic inhibitor of vascular smooth muscle cells |
US5280040A (en) * | 1993-03-11 | 1994-01-18 | Zymogenetics, Inc. | Methods for reducing bone loss using centchroman derivatives |
US5389646A (en) * | 1993-12-30 | 1995-02-14 | Zymogenetics, Inc. | Methods for treatment and prevention of bone loss using 2,3-benzopyrans |
US5407955A (en) * | 1994-02-18 | 1995-04-18 | Eli Lilly And Company | Methods for lowering serum cholesterol and inhibiting smooth muscle cell proliferation, restenosis, endometriosis, and uterine fibroid disease |
US5637598A (en) * | 1994-11-18 | 1997-06-10 | Eli Lilly And Company | Methods of inhibiting bone loss |
JPH10511960A (ja) * | 1995-01-13 | 1998-11-17 | ノボ ノルディスク アクティーゼルスカブ | 特発性の又は生理学的な女性化乳房の治療又は予防のための医薬製剤の製造のための3,4−ジフェニル・クロマンの使用 |
TW448046B (en) * | 1995-01-20 | 2001-08-01 | Novo Nordisk As | Use of 3,4-diphenyl chromans for the manufacture of a pharmaceutical composition for the treatment or prophylaxis of obesity |
KR19980701548A (ko) * | 1995-01-20 | 1998-05-15 | 슈타르 피아 | 혈관확장치료 또는 예방용 약학적 조성물의 제조를 위한 3,4-디페닐크로만의 이용(use of 3,4-diphenyl chromans for the manufacture of a pharmaceutical composition for vasodilatory treatment or prophylaxis) |
CZ212097A3 (en) * | 1995-01-20 | 1997-11-12 | Novo Nordisk As | Use of 3,4-diphenylchromans for preparing a medicament intended for treating or prophylaxis of cerebral degenerative diseases |
US20030083733A1 (en) * | 1997-10-10 | 2003-05-01 | Neorx Corporation | Therapeutic inhibitor of vascular smooth muscle cells |
US6099562A (en) * | 1996-06-13 | 2000-08-08 | Schneider (Usa) Inc. | Drug coating with topcoat |
US20020091433A1 (en) * | 1995-04-19 | 2002-07-11 | Ni Ding | Drug release coated stent |
US5837313A (en) * | 1995-04-19 | 1998-11-17 | Schneider (Usa) Inc | Drug release stent coating process |
US6008208A (en) * | 1995-10-23 | 1999-12-28 | Osteoscreen, Inc. | Compositions and methods for treating bone deficit conditions |
AU706262B2 (en) * | 1995-10-23 | 1999-06-10 | Osteoscreen, Inc. | Compositions and methods for treating bone deficit conditions |
US5883118A (en) * | 1996-01-11 | 1999-03-16 | Nova Nordisk A/S | Prostatic carcinoma |
US5859045A (en) * | 1996-05-08 | 1999-01-12 | Novo Nordisk A/S Novo Alle | Crystalline -! 3R 4R-trans-7 methoxy 2,2-dimethyl1-3-phenyl 1-4 4-12 pyrrolidin-1 -Y1!ethoxyl 1!chromane hydrogen fumarate |
HUP9901738A3 (en) * | 1996-05-08 | 2000-12-28 | Novo Nordisk As | Crystalline(-)-3r,4r-trans-7-methoxy-2,2-dimethyl-3-phenyl-4-{4-[2-(pyrrolidin-1-yl)ethoxy]phenyl}chromane, hydrogen fumarate, medicament containing the same and method for producing them |
US5756539A (en) * | 1996-07-11 | 1998-05-26 | Novo Nordis A/S | 3, 4-diphenyl chromans for inhibiting one or more psychiatric disorders |
US5780502A (en) * | 1996-07-12 | 1998-07-14 | Novo Nordisk A/S | Use of 3,4-diphenyl chromans for the manufacture of a pharmaceutical composition for inhibiting one or more symptoms of premenstrual syndrome |
US5990169A (en) * | 1996-10-23 | 1999-11-23 | Zymogenetics, Inc. | Compositions and methods for treating bone deficit conditions |
US6342514B1 (en) | 1996-10-23 | 2002-01-29 | Zymogenetics, Inc. | Compositions and methods for treating bone deficit conditions |
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US6153631A (en) * | 1996-10-23 | 2000-11-28 | Zymogenetics, Inc. | Compositions and methods for treating bone deficit conditions |
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WO1998018772A1 (en) * | 1996-10-28 | 1998-05-07 | Novo Nordisk A/S | NOVEL cis-3,4-CHROMAN DERIVATIVES USEFUL IN THE PREVENTION OR TREATMENT OF ESTROGEN RELATED DISEASES OR SYNDROMES |
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WO1998018779A1 (en) * | 1996-10-28 | 1998-05-07 | Novo Nordisk A/S | Novel cis-3,4-chroman derivatives useful in the prevention or treatment of estrogen related diseases or syndromes |
US5985306A (en) * | 1996-10-28 | 1999-11-16 | Novo Nordisk A/S | (+)-enantiomers of cis-3,4-chroman derivatives useful in prevention or treatment of estrogen diseases or syndromes |
JP2001502709A (ja) * | 1996-10-28 | 2001-02-27 | ノボ ノルディスク アクティーゼルスカブ | エストロゲン関連疾患または症候群の予防または治療に有用な新規なシス―3,4―クロマン誘導体 |
US5994390A (en) * | 1996-10-28 | 1999-11-30 | Novo Nordisk | Trans-3,4-chroman derivatives useful in the prevention or treatment of estrogen related diseases or syndromes |
JP2001504502A (ja) * | 1996-11-28 | 2001-04-03 | ノボ ノルディスク アクティー ゼルスカブ | 薬学的製剤 |
US5977158A (en) * | 1996-11-28 | 1999-11-02 | Novo Nordisk A/S | Pharmaceutical formulations comprising levormeloxifene compounds |
US6080779A (en) * | 1996-12-13 | 2000-06-27 | Osteoscreen, Inc. | Compositions and methods for stimulating bone growth |
CA2274789A1 (en) * | 1996-12-13 | 1998-06-18 | Zymogenetics, Inc. | Compositions and methods for stimulating bone growth |
US6376476B1 (en) * | 1996-12-13 | 2002-04-23 | Zymogenetics Corporation | Isoprenoid pathway inhibitors for stimulating bone growth |
WO1998037884A1 (en) * | 1997-02-27 | 1998-09-03 | Novo Nordisk A/S | Inclusion complexes in aqueous solution |
WO1998046588A2 (en) | 1997-04-11 | 1998-10-22 | Neorx Corporation | Compounds and therapies for the prevention of vascular and non-vascular pathologies |
US6372776B2 (en) * | 1997-06-12 | 2002-04-16 | Novo Nordisk A/S | Crystalline(−)-3R,4R-trans-7-methoxy-2,2-dimethyl-3-phenyl-4-{4-[2-(pyrrolidin-1-yl)ethoxy]phenyl}chromane, hydrogen maleate |
US6649631B1 (en) | 1997-10-23 | 2003-11-18 | The Board Of Regents Of The University Of Texas System | Compositions and methods for treating bone deficit conditions |
ZA989763B (en) * | 1997-11-07 | 1999-05-07 | Novo Nordisk As | Pharmaceutical composition comprising levormeloxifene in low dose |
AU1143899A (en) * | 1997-11-10 | 1999-05-31 | Novo Nordisk A/S | Transdermal delivery of 3,4-diarylchromans |
US6902721B1 (en) | 1998-07-10 | 2005-06-07 | Osteoscreen, Inc. | Inhibitors of proteasomal activity for stimulating bone growth |
US6462019B1 (en) | 1998-07-10 | 2002-10-08 | Osteoscreen, Inc. | Inhibitors of proteasomal activity and production for stimulating bone growth |
US6838436B1 (en) | 1998-07-10 | 2005-01-04 | Osteoscreen Inc. | Inhibitors of proteasomal activity for stimulating bone growth |
US6525084B2 (en) * | 1998-07-23 | 2003-02-25 | Novo Nordisk A/S | Stable pharmaceutical formulation |
US7214706B2 (en) | 2000-03-01 | 2007-05-08 | Akzo Nobel N.V. | Chroman derivatives as estrogenic compounds |
EP1281710A1 (en) * | 2001-08-03 | 2003-02-05 | CHIESI FARMACEUTICI S.p.A. | 2H-1-benzopyran derivatives, processes for their preparation and pharmaceutical compositions thereof |
ATE286894T1 (de) * | 2001-01-24 | 2005-01-15 | Chiesi Farma Spa | 2h-1-benzopyran-derivate, prozesse zu ihrer herstellung und pharmazeutische zusammensetzungen |
ATE286893T1 (de) * | 2001-01-24 | 2005-01-15 | Chiesi Farma Spa | 2h-1-benzopyran-derivative, prozesse zu ihrer herstellung und pharmazeutische zusammensetzungen |
US6613083B2 (en) * | 2001-05-02 | 2003-09-02 | Eckhard Alt | Stent device and method |
US20030181374A1 (en) * | 2002-01-14 | 2003-09-25 | Mundy Gregory R. | Methods and compositions for stimulating bone growth using inhibitors of microtubule assembly |
AU2003231255A1 (en) * | 2002-05-02 | 2003-12-31 | Osteoscreen, Inc. | Methods and compositions for stimulating bone growth using nitric oxide releasing bisphosphonate conjugates (no-bisphosphonate) |
US7041309B2 (en) * | 2002-06-13 | 2006-05-09 | Neuropro Technologies, Inc. | Spinal fusion using an HMG-CoA reductase inhibitor |
WO2004091626A1 (en) * | 2003-04-07 | 2004-10-28 | Osteoscreen, Inc. | Bone growth stimulation with no/statin and other no modulating combinations |
ATE532777T1 (de) | 2004-09-21 | 2011-11-15 | Marshall Edwards Inc | Substituierte chromanderivate, medikamente und anwendungen in der therapie |
US8080675B2 (en) | 2004-09-21 | 2011-12-20 | Marshall Edwards, Inc. | Chroman derivatives, medicaments and use in therapy |
EP2217260B1 (en) * | 2007-12-04 | 2016-11-09 | Ben-Gurion University Of The Negev Research And Development Authority | Amphiphilic peptide matrices for treatment of osteoporosis |
EP2635121B1 (en) | 2010-11-01 | 2020-01-08 | MEI Pharma, Inc. | Isoflavonoid compounds and methods for the treatment of cancer |
NZ711603A (en) | 2014-02-07 | 2017-05-26 | Novogen ltd | Functionalised benzopyran compounds and use thereof |
PL3253208T3 (pl) | 2015-02-02 | 2021-11-08 | Mei Pharma, Inc. | Terapie kombinowane do zastosowania w leczeniu nowotworu piersi |
LU100182B1 (en) * | 2017-04-06 | 2018-10-15 | Univ Hamburg Eppendorf Uke | Therapeutic use of microRNA 19A/19B |
Family Cites Families (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3340276A (en) * | 1964-04-01 | 1967-09-05 | Ciba Geigy Corp | 3, 4-diphenyl-chromans |
US3822287A (en) * | 1969-04-17 | 1974-07-02 | Rexall Drug Chemical | Process for preparation of substituted 3,4-(diphenyl)chromans |
US4210644A (en) * | 1978-02-23 | 1980-07-01 | The Johns Hopkins University | Male contraception |
US4447622A (en) * | 1981-09-22 | 1984-05-08 | Council Of Scientific And Industrial Research Rafi Marg | Preparation of l- and d-isomers of dl-3,4-trans-2,2-disubstituted-3,4-diarylchromans and derivatives thereof |
US4489056A (en) * | 1982-06-30 | 1984-12-18 | Merck & Co., Inc. | Acid anhydrides as rate controlling agent for the erosion of polymers which latter polymers have beneficial substances dispersed throughout their matrix or where the polymer matrix surrounds the beneficial substance |
JPS6054379A (ja) * | 1983-09-05 | 1985-03-28 | Takeda Chem Ind Ltd | 新規4h−1−ベンゾピラン−4−オン誘導体,その製法および用途 |
US4644012A (en) * | 1983-12-21 | 1987-02-17 | Takeda Chemical Industries, Ltd. | Treatment for osteoporosis |
US4902679A (en) * | 1985-12-13 | 1990-02-20 | Norwich Eaton Pharmaceuticals, Inc. | Methods of treating diseases with certain geminal diphosphonates |
PH24144A (en) * | 1987-06-03 | 1990-03-22 | Erba Carlo Spa | A method of treating nephropathies using n-imidazolyl derivatives of bicyclic compounds |
US5015661A (en) * | 1988-08-09 | 1991-05-14 | Hoffmann-La Roche Inc. | Chromanes and their pharmaceutical compositions and methods |
US5063234A (en) * | 1990-05-25 | 1991-11-05 | Eli Lilly And Company | Method of inhibiting demineralization of bone |
JP3502403B2 (ja) * | 1991-12-16 | 2004-03-02 | アベンティス ファーマ株式会社 | 骨吸収抑制剤 |
US5280040A (en) * | 1993-03-11 | 1994-01-18 | Zymogenetics, Inc. | Methods for reducing bone loss using centchroman derivatives |
-
1993
- 1993-03-11 US US08/029,729 patent/US5280040A/en not_active Expired - Lifetime
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1994
- 1994-01-13 RU RU95122775/14A patent/RU2166940C2/ru not_active IP Right Cessation
- 1994-01-13 JP JP6519963A patent/JP2834581B2/ja not_active Expired - Fee Related
- 1994-01-13 AT AT94909463T patent/ATE178488T1/de not_active IP Right Cessation
- 1994-01-13 BR BR9405843A patent/BR9405843A/pt not_active Application Discontinuation
- 1994-01-13 DE DE69417733T patent/DE69417733T2/de not_active Expired - Fee Related
- 1994-01-13 SG SG1996007639A patent/SG65584A1/en unknown
- 1994-01-13 KR KR1019950703749A patent/KR100263009B1/ko not_active IP Right Cessation
- 1994-01-13 NZ NZ262569A patent/NZ262569A/xx unknown
- 1994-01-13 ES ES94909463T patent/ES2131678T3/es not_active Expired - Lifetime
- 1994-01-13 US US08/180,728 patent/US5464862A/en not_active Expired - Fee Related
- 1994-01-13 EP EP94909463A patent/EP0688214B1/en not_active Expired - Lifetime
- 1994-01-13 HU HU9502624A patent/HUT74575A/hu unknown
- 1994-01-13 CZ CZ19952320A patent/CZ287603B6/cs not_active IP Right Cessation
- 1994-01-13 AU AU62302/94A patent/AU674394B2/en not_active Ceased
- 1994-01-13 WO PCT/US1994/000633 patent/WO1994020098A1/en active IP Right Grant
- 1994-01-13 CA CA002157879A patent/CA2157879C/en not_active Expired - Fee Related
- 1994-01-13 DK DK94909463T patent/DK0688214T3/da active
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1995
- 1995-09-08 NO NO953542A patent/NO309361B1/no not_active IP Right Cessation
-
1997
- 1997-03-19 AU AU16394/97A patent/AU695497B2/en not_active Ceased
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1999
- 1999-04-30 GR GR990401210T patent/GR3030128T3/el unknown
Also Published As
Publication number | Publication date |
---|---|
AU674394B2 (en) | 1996-12-19 |
AU695497B2 (en) | 1998-08-13 |
DE69417733D1 (de) | 1999-05-12 |
KR100263009B1 (ko) | 2000-08-01 |
AU6230294A (en) | 1994-09-26 |
RU2166940C2 (ru) | 2001-05-20 |
EP0688214B1 (en) | 1999-04-07 |
HUT74575A (en) | 1997-01-28 |
CA2157879A1 (en) | 1994-09-12 |
JPH08506346A (ja) | 1996-07-09 |
ES2131678T3 (es) | 1999-08-01 |
CZ232095A3 (en) | 1996-04-17 |
EP0688214A1 (en) | 1995-12-27 |
DK0688214T3 (da) | 2000-10-09 |
WO1994020098A1 (en) | 1994-09-15 |
US5464862A (en) | 1995-11-07 |
BR9405843A (pt) | 1996-01-16 |
DE69417733T2 (de) | 1999-09-16 |
NZ262569A (en) | 1997-08-22 |
SG65584A1 (en) | 1999-06-22 |
US5280040A (en) | 1994-01-18 |
JP2834581B2 (ja) | 1998-12-09 |
CZ287603B6 (en) | 2001-01-17 |
HU9502624D0 (en) | 1995-11-28 |
CA2157879C (en) | 2000-08-29 |
AU1639497A (en) | 1997-05-22 |
NO953542D0 (no) | 1995-09-08 |
NO953542L (no) | 1995-09-08 |
KR960700708A (ko) | 1996-02-24 |
ATE178488T1 (de) | 1999-04-15 |
GR3030128T3 (en) | 1999-07-30 |
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