AU4771997A - Novel (+)-enantiomers of (cis)-3,4-chroman derivatives useful in the preve ntion or treatment of estrogen related diseases or syndromes - Google Patents
Novel (+)-enantiomers of (cis)-3,4-chroman derivatives useful in the preve ntion or treatment of estrogen related diseases or syndromesInfo
- Publication number
- AU4771997A AU4771997A AU47719/97A AU4771997A AU4771997A AU 4771997 A AU4771997 A AU 4771997A AU 47719/97 A AU47719/97 A AU 47719/97A AU 4771997 A AU4771997 A AU 4771997A AU 4771997 A AU4771997 A AU 4771997A
- Authority
- AU
- Australia
- Prior art keywords
- phenyl
- hydroxy
- formula
- compound
- chromane
- Prior art date
- 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
Links
- 239000000262 estrogen Substances 0.000 title claims description 61
- 229940011871 estrogen Drugs 0.000 title claims description 60
- 238000011282 treatment Methods 0.000 title claims description 30
- 230000002265 prevention Effects 0.000 title claims description 25
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims description 17
- 201000010099 disease Diseases 0.000 title claims description 15
- 208000011580 syndromic disease Diseases 0.000 title claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 191
- VZWXIQHBIQLMPN-UHFFFAOYSA-N chromane Chemical compound C1=CC=C2CCCOC2=C1 VZWXIQHBIQLMPN-UHFFFAOYSA-N 0.000 claims description 85
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 59
- 239000000203 mixture Substances 0.000 claims description 43
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 36
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 claims description 24
- 125000001424 substituent group Chemical group 0.000 claims description 23
- 239000003795 chemical substances by application Substances 0.000 claims description 22
- 229910052736 halogen Inorganic materials 0.000 claims description 21
- 150000002367 halogens Chemical class 0.000 claims description 21
- -1 methoxy, hydroxy Chemical group 0.000 claims description 20
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 19
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 18
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 18
- 238000010511 deprotection reaction Methods 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 16
- 229910052760 oxygen Inorganic materials 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 229910052717 sulfur Inorganic materials 0.000 claims description 12
- 206010065687 Bone loss Diseases 0.000 claims description 11
- 230000004927 fusion Effects 0.000 claims description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 9
- 208000001132 Osteoporosis Diseases 0.000 claims description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- 229920006395 saturated elastomer Polymers 0.000 claims description 9
- 208000024827 Alzheimer disease Diseases 0.000 claims description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 8
- 125000005842 heteroatom Chemical group 0.000 claims description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims description 8
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- 206010020112 Hirsutism Diseases 0.000 claims description 7
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- 206010000496 acne Diseases 0.000 claims description 7
- 230000006408 female gonad development Effects 0.000 claims description 7
- 230000006651 lactation Effects 0.000 claims description 7
- DYOPGFDNUDULHG-BDYUSTAISA-N (3r,4s)-4-[4-(2-pyrrolidin-1-ylethoxy)phenyl]-3-[4-(trifluoromethyl)phenyl]-3,4-dihydro-2h-chromen-7-ol Chemical compound C1([C@H]2[C@H](C3=CC=C(C=C3OC2)O)C=2C=CC(OCCN3CCCC3)=CC=2)=CC=C(C(F)(F)F)C=C1 DYOPGFDNUDULHG-BDYUSTAISA-N 0.000 claims description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
- 230000002152 alkylating effect Effects 0.000 claims description 6
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 claims description 6
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- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 238000006880 cross-coupling reaction Methods 0.000 claims description 5
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- 201000000980 schizophrenia Diseases 0.000 claims description 5
- 229910052727 yttrium Inorganic materials 0.000 claims description 5
- AARXKTUFDDEKCL-BDYUSTAISA-N (3r,4s)-3-(3-hydroxyphenyl)-4-[4-(2-pyrrolidin-1-ylethoxy)phenyl]-3,4-dihydro-2h-chromen-7-ol Chemical compound OC1=CC=CC([C@H]2[C@H](C3=CC=C(O)C=C3OC2)C=2C=CC(OCCN3CCCC3)=CC=2)=C1 AARXKTUFDDEKCL-BDYUSTAISA-N 0.000 claims description 4
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 4
- IBYHHJPAARCAIE-UHFFFAOYSA-N 1-bromo-2-chloroethane Chemical compound ClCCBr IBYHHJPAARCAIE-UHFFFAOYSA-N 0.000 claims description 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 4
- 239000007818 Grignard reagent Substances 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 claims description 4
- 239000003638 chemical reducing agent Substances 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 208000010877 cognitive disease Diseases 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 150000004795 grignard reagents Chemical class 0.000 claims description 4
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- PZCIPDMAXDPGEV-XCZPVHLTSA-N (3r,4s)-3-(4-methylphenyl)-4-[4-(2-pyrrolidin-1-ylethoxy)phenyl]-3,4-dihydro-2h-chromen-7-ol Chemical compound C1=CC(C)=CC=C1[C@H]1[C@@H](C=2C=CC(OCCN3CCCC3)=CC=2)C2=CC=C(O)C=C2OC1 PZCIPDMAXDPGEV-XCZPVHLTSA-N 0.000 claims description 3
- 239000007819 coupling partner Substances 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 150000002170 ethers Chemical class 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- GTQHJCOHNAFHRE-UHFFFAOYSA-N 1,10-dibromodecane Chemical compound BrCCCCCCCCCCBr GTQHJCOHNAFHRE-UHFFFAOYSA-N 0.000 claims description 2
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 claims description 2
- ULTHEAFYOOPTTB-UHFFFAOYSA-N 1,4-dibromobutane Chemical compound BrCCCCBr ULTHEAFYOOPTTB-UHFFFAOYSA-N 0.000 claims description 2
- SGRHVVLXEBNBDV-UHFFFAOYSA-N 1,6-dibromohexane Chemical compound BrCCCCCCBr SGRHVVLXEBNBDV-UHFFFAOYSA-N 0.000 claims description 2
- DKEGCUDAFWNSSO-UHFFFAOYSA-N 1,8-dibromooctane Chemical compound BrCCCCCCCCBr DKEGCUDAFWNSSO-UHFFFAOYSA-N 0.000 claims description 2
- GIGRWGTZFONRKA-UHFFFAOYSA-N 1-(bromomethyl)-4-methoxybenzene Chemical compound COC1=CC=C(CBr)C=C1 GIGRWGTZFONRKA-UHFFFAOYSA-N 0.000 claims description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
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- 229930040373 Paraformaldehyde Natural products 0.000 claims description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- 239000003433 contraceptive agent Substances 0.000 claims description 2
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- 150000004678 hydrides Chemical class 0.000 claims description 2
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- 230000000802 nitrating effect Effects 0.000 claims description 2
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- 239000008024 pharmaceutical diluent Substances 0.000 claims description 2
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- WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 2
- FEVZKAOFFCUDLI-BDYUSTAISA-N (3r,4s)-3-phenyl-4-[4-(2-pyrrolidin-1-ylethoxy)phenyl]-3,4-dihydro-2h-chromen-7-ol Chemical compound C1([C@H]2[C@H](C3=CC=C(C=C3OC2)O)C=2C=CC(OCCN3CCCC3)=CC=2)=CC=CC=C1 FEVZKAOFFCUDLI-BDYUSTAISA-N 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
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- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
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- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/74—Benzo[b]pyrans, hydrogenated in the carbocyclic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Rheumatology (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Diabetes (AREA)
- Endocrinology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrane Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DK120296 | 1996-10-28 | ||
| DK1202/96 | 1996-10-28 | ||
| PCT/DK1997/000482 WO1998018775A1 (fr) | 1996-10-28 | 1997-10-28 | Nouveaux (+)-enantiomeres de derives de cis-3,4-chromane utiles pour la prevention ou le traitement de maladies ou de syndromes relatifs aux oestrogenes |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU97336/01A Division AU9733601A (en) | 1996-10-28 | 2001-12-19 | Novel (+)-enantiomers of cis-3,4-chroman derivatives useful in the prevention or treatment of estrogen related diseases or syndromes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AU4771997A true AU4771997A (en) | 1998-05-22 |
Family
ID=8102133
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU47719/97A Abandoned AU4771997A (en) | 1996-10-28 | 1997-10-28 | Novel (+)-enantiomers of (cis)-3,4-chroman derivatives useful in the preve ntion or treatment of estrogen related diseases or syndromes |
Country Status (8)
| Country | Link |
|---|---|
| EP (1) | EP0934298A1 (fr) |
| JP (1) | JP2001502707A (fr) |
| AU (1) | AU4771997A (fr) |
| CA (1) | CA2269970A1 (fr) |
| IL (1) | IL129624A0 (fr) |
| NO (1) | NO992008L (fr) |
| WO (1) | WO1998018775A1 (fr) |
| ZA (1) | ZA979644B (fr) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK1140889T3 (da) * | 1998-12-30 | 2003-12-22 | Signal Pharm Inc | Forbindelser og metoder til modulation af estrogen-receptorer |
| CO5251465A1 (es) | 2000-01-26 | 2003-02-28 | Pfizer Prod Inc | Composiciones y procedimientos para tratar la osteoporosis y reducir el colesterol |
| US8080675B2 (en) | 2004-09-21 | 2011-12-20 | Marshall Edwards, Inc. | Chroman derivatives, medicaments and use in therapy |
| CA2581316C (fr) | 2004-09-21 | 2013-09-10 | Novogen Research Pty Ltd | Derives de chromane substitues, medicaments et utilisation a des fins therapeutiques |
| WO2008113100A1 (fr) * | 2007-03-16 | 2008-09-25 | Novogen Research Pty Ltd | Procédé d'induction d'autophagie |
| EP2635273B1 (fr) | 2010-11-01 | 2020-01-08 | MEI Pharma, Inc. | Compositions d'isoflavonoïdes et méthodes de traitement du cancer |
| CN116139125A (zh) | 2015-02-02 | 2023-05-23 | 梅制药公司 | 联合治疗 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3340276A (en) * | 1964-04-01 | 1967-09-05 | Ciba Geigy Corp | 3, 4-diphenyl-chromans |
| DE1543749A1 (de) * | 1966-02-16 | 1969-12-11 | Merck Ag E | Verfahren zur Herstellung von 3,4-cis-4-Aryl-isoflavanen |
| US5280040A (en) * | 1993-03-11 | 1994-01-18 | Zymogenetics, Inc. | Methods for reducing bone loss using centchroman derivatives |
| HUP9702244A3 (en) * | 1995-01-13 | 1999-12-28 | Novo Nordisk As | Use of 3,4-diphenyl chromans for manufacture of a pharmaceutical composition for treatment or prophylaxis of gynaecological disorders |
-
1997
- 1997-10-18 ZA ZA9709644A patent/ZA979644B/xx unknown
- 1997-10-28 CA CA002269970A patent/CA2269970A1/fr not_active Abandoned
- 1997-10-28 JP JP10519941A patent/JP2001502707A/ja active Pending
- 1997-10-28 EP EP97910263A patent/EP0934298A1/fr not_active Withdrawn
- 1997-10-28 IL IL12962497A patent/IL129624A0/xx unknown
- 1997-10-28 AU AU47719/97A patent/AU4771997A/en not_active Abandoned
- 1997-10-28 WO PCT/DK1997/000482 patent/WO1998018775A1/fr not_active Ceased
-
1999
- 1999-04-27 NO NO992008A patent/NO992008L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| JP2001502707A (ja) | 2001-02-27 |
| CA2269970A1 (fr) | 1998-05-07 |
| ZA979644B (en) | 1998-04-28 |
| NO992008D0 (no) | 1999-04-27 |
| EP0934298A1 (fr) | 1999-08-11 |
| NO992008L (no) | 1999-06-25 |
| IL129624A0 (en) | 2000-02-29 |
| WO1998018775A1 (fr) | 1998-05-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK5 | Application lapsed section 142(2)(e) - patent request and compl. specification not accepted |