JP2007508394A - フェニルピペラジンシクロアルカノール誘導体およびその使用方法 - Google Patents
フェニルピペラジンシクロアルカノール誘導体およびその使用方法 Download PDFInfo
- Publication number
- JP2007508394A JP2007508394A JP2006535601A JP2006535601A JP2007508394A JP 2007508394 A JP2007508394 A JP 2007508394A JP 2006535601 A JP2006535601 A JP 2006535601A JP 2006535601 A JP2006535601 A JP 2006535601A JP 2007508394 A JP2007508394 A JP 2007508394A
- Authority
- JP
- Japan
- Prior art keywords
- piperazin
- ylethyl
- chlorophenyl
- subject
- cyclobutanol
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims abstract description 80
- YZTJYBJCZXZGCT-UHFFFAOYSA-N phenylpiperazine Chemical compound C1CNCCN1C1=CC=CC=C1 YZTJYBJCZXZGCT-UHFFFAOYSA-N 0.000 title abstract description 5
- 208000024891 symptom Diseases 0.000 claims abstract description 61
- 208000002193 Pain Diseases 0.000 claims abstract description 55
- 230000036407 pain Effects 0.000 claims abstract description 48
- 239000000203 mixture Substances 0.000 claims abstract description 29
- 230000001457 vasomotor Effects 0.000 claims abstract description 28
- 208000001640 Fibromyalgia Diseases 0.000 claims abstract description 18
- 201000001880 Sexual dysfunction Diseases 0.000 claims abstract description 16
- 231100000872 sexual dysfunction Toxicity 0.000 claims abstract description 16
- 208000000921 Urge Urinary Incontinence Diseases 0.000 claims abstract description 10
- 230000002496 gastric effect Effects 0.000 claims abstract description 10
- 230000000407 monoamine reuptake Effects 0.000 claims abstract description 10
- 208000032131 Diabetic Neuropathies Diseases 0.000 claims abstract description 9
- 208000012902 Nervous system disease Diseases 0.000 claims abstract description 9
- 230000001668 ameliorated effect Effects 0.000 claims abstract description 9
- 208000024714 major depressive disease Diseases 0.000 claims abstract description 9
- 206010046494 urge incontinence Diseases 0.000 claims abstract description 8
- 150000001875 compounds Chemical class 0.000 claims description 112
- -1 CF 3 Chemical group 0.000 claims description 109
- 150000003839 salts Chemical class 0.000 claims description 43
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 27
- 125000004432 carbon atom Chemical group C* 0.000 claims description 25
- 208000035475 disorder Diseases 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 230000009245 menopause Effects 0.000 claims description 15
- 125000000623 heterocyclic group Chemical group 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 206010008874 Chronic Fatigue Syndrome Diseases 0.000 claims description 8
- 208000029766 myalgic encephalomeyelitis/chronic fatigue syndrome Diseases 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 206010066218 Stress Urinary Incontinence Diseases 0.000 claims description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- PZQVDLYPNAADGQ-UHFFFAOYSA-N 1-[1-(3-chlorophenyl)-2-piperazin-1-ylethyl]cyclohexan-1-ol Chemical compound C1CNCCN1CC(C=1C=C(Cl)C=CC=1)C1(O)CCCCC1 PZQVDLYPNAADGQ-UHFFFAOYSA-N 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
- 125000006564 (C4-C8) cycloalkyl group Chemical group 0.000 claims description 4
- CZRBZQHNTQGFDV-UHFFFAOYSA-N 1-[1-(3-bromophenyl)-2-piperazin-1-ylethyl]cyclooctan-1-ol Chemical compound C1CNCCN1CC(C=1C=C(Br)C=CC=1)C1(O)CCCCCCC1 CZRBZQHNTQGFDV-UHFFFAOYSA-N 0.000 claims description 4
- PIBZTCVMCNNFRR-UHFFFAOYSA-N 1-[1-(3-fluorophenyl)-2-piperazin-1-ylethyl]cyclohexan-1-ol Chemical compound C1CNCCN1CC(C=1C=C(F)C=CC=1)C1(O)CCCCC1 PIBZTCVMCNNFRR-UHFFFAOYSA-N 0.000 claims description 4
- REBCRUZAHKPPJG-UHFFFAOYSA-N 1-[1-(4-bromophenyl)-2-piperazin-1-ylethyl]cyclobutan-1-ol Chemical compound C1CNCCN1CC(C=1C=CC(Br)=CC=1)C1(O)CCC1 REBCRUZAHKPPJG-UHFFFAOYSA-N 0.000 claims description 4
- KHWNQEDSMGUKSX-UHFFFAOYSA-N 1-[1-(4-chlorophenyl)-2-piperazin-1-ylethyl]cyclohexan-1-ol Chemical compound C1CNCCN1CC(C=1C=CC(Cl)=CC=1)C1(O)CCCCC1 KHWNQEDSMGUKSX-UHFFFAOYSA-N 0.000 claims description 4
- IQHHTOSZORUSLE-UHFFFAOYSA-N 1-[1-(4-fluorophenyl)-2-piperazin-1-ylethyl]cyclohexan-1-ol Chemical compound C1CNCCN1CC(C=1C=CC(F)=CC=1)C1(O)CCCCC1 IQHHTOSZORUSLE-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000004423 acyloxy group Chemical group 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 150000002431 hydrogen Chemical group 0.000 claims description 4
- 208000019116 sleep disease Diseases 0.000 claims description 4
- DGBKDBRUKWAZBY-UHFFFAOYSA-N 1-[1-(3-bromophenyl)-2-(4-methylpiperazin-1-yl)ethyl]cyclooctan-1-ol Chemical compound C1CN(C)CCN1CC(C1(O)CCCCCCC1)C1=CC=CC(Br)=C1 DGBKDBRUKWAZBY-UHFFFAOYSA-N 0.000 claims description 3
- ZFQGQANQGWASIE-UHFFFAOYSA-N 1-[1-(3-chlorophenyl)-2-(4-methylpiperazin-1-yl)ethyl]cyclooctan-1-ol Chemical compound C1CN(C)CCN1CC(C1(O)CCCCCCC1)C1=CC=CC(Cl)=C1 ZFQGQANQGWASIE-UHFFFAOYSA-N 0.000 claims description 3
- SBXWKBLGYGJAMJ-MCPYQZEQSA-N 1-[1-(3-chlorophenyl)-2-[(3r,5s)-3,5-dimethylpiperazin-1-yl]ethyl]cyclohexan-1-ol Chemical compound C1[C@@H](C)N[C@@H](C)CN1CC(C1(O)CCCCC1)C1=CC=CC(Cl)=C1 SBXWKBLGYGJAMJ-MCPYQZEQSA-N 0.000 claims description 3
- RMNOTTSKUONNGC-UHFFFAOYSA-N 1-[1-(3-chlorophenyl)-2-piperazin-1-ylethyl]cyclobutan-1-ol Chemical compound C1CNCCN1CC(C=1C=C(Cl)C=CC=1)C1(O)CCC1 RMNOTTSKUONNGC-UHFFFAOYSA-N 0.000 claims description 3
- DIMZLFDDDJZTNC-UHFFFAOYSA-N 1-[1-(3-chlorophenyl)-2-piperazin-1-ylethyl]cyclooctan-1-ol Chemical compound C1CNCCN1CC(C=1C=C(Cl)C=CC=1)C1(O)CCCCCCC1 DIMZLFDDDJZTNC-UHFFFAOYSA-N 0.000 claims description 3
- HPBLUEOXHZOXFX-UHFFFAOYSA-N 1-[1-(4-chlorophenyl)-2-piperazin-1-ylethyl]cyclobutan-1-ol Chemical compound C1CNCCN1CC(C=1C=CC(Cl)=CC=1)C1(O)CCC1 HPBLUEOXHZOXFX-UHFFFAOYSA-N 0.000 claims description 3
- KZMYISUBTLBMKL-UHFFFAOYSA-N 1-[2-(4-methylpiperazin-1-yl)-1-[3-(trifluoromethyl)phenyl]ethyl]cyclobutan-1-ol Chemical compound C1CN(C)CCN1CC(C1(O)CCC1)C1=CC=CC(C(F)(F)F)=C1 KZMYISUBTLBMKL-UHFFFAOYSA-N 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 208000022170 stress incontinence Diseases 0.000 claims description 3
- PZQVDLYPNAADGQ-KRWDZBQOSA-N 1-[(1r)-1-(3-chlorophenyl)-2-piperazin-1-ylethyl]cyclohexan-1-ol Chemical compound OC1([C@@H](CN2CCNCC2)C=2C=C(Cl)C=CC=2)CCCCC1 PZQVDLYPNAADGQ-KRWDZBQOSA-N 0.000 claims description 2
- PZQVDLYPNAADGQ-QGZVFWFLSA-N 1-[(1s)-1-(3-chlorophenyl)-2-piperazin-1-ylethyl]cyclohexan-1-ol Chemical compound OC1([C@H](CN2CCNCC2)C=2C=C(Cl)C=CC=2)CCCCC1 PZQVDLYPNAADGQ-QGZVFWFLSA-N 0.000 claims description 2
- QFIJRJZGJBEPSZ-UHFFFAOYSA-N 1-[1-(2-bromophenyl)-2-piperazin-1-ylethyl]cyclohexan-1-ol Chemical compound C1CNCCN1CC(C=1C(=CC=CC=1)Br)C1(O)CCCCC1 QFIJRJZGJBEPSZ-UHFFFAOYSA-N 0.000 claims description 2
- FBPIYNSAIXRAKI-UHFFFAOYSA-N 1-[1-(2-fluorophenyl)-2-(4-methylpiperazin-1-yl)ethyl]cyclobutan-1-ol Chemical compound C1CN(C)CCN1CC(C1(O)CCC1)C1=CC=CC=C1F FBPIYNSAIXRAKI-UHFFFAOYSA-N 0.000 claims description 2
- BLTKKNKJEHRTJP-UHFFFAOYSA-N 1-[1-(2-fluorophenyl)-2-piperazin-1-ylethyl]cyclobutan-1-ol Chemical compound C1CNCCN1CC(C=1C(=CC=CC=1)F)C1(O)CCC1 BLTKKNKJEHRTJP-UHFFFAOYSA-N 0.000 claims description 2
- LBHZTGKCTKOYTN-UHFFFAOYSA-N 1-[1-(2-fluorophenyl)-2-piperazin-1-ylethyl]cyclohexan-1-ol Chemical compound C1CNCCN1CC(C=1C(=CC=CC=1)F)C1(O)CCCCC1 LBHZTGKCTKOYTN-UHFFFAOYSA-N 0.000 claims description 2
- OPAKGKQKMQGOGL-UHFFFAOYSA-N 1-[1-(3,4-dichlorophenyl)-2-piperazin-1-ylethyl]cyclohexan-1-ol Chemical compound C1CNCCN1CC(C=1C=C(Cl)C(Cl)=CC=1)C1(O)CCCCC1 OPAKGKQKMQGOGL-UHFFFAOYSA-N 0.000 claims description 2
- IAXITOGKMSXBJM-UHFFFAOYSA-N 1-[1-(3-bromo-4-methoxyphenyl)-2-piperazin-1-ylethyl]cyclooctan-1-ol Chemical compound C1=C(Br)C(OC)=CC=C1C(C1(O)CCCCCCC1)CN1CCNCC1 IAXITOGKMSXBJM-UHFFFAOYSA-N 0.000 claims description 2
- BSNFRMQEINNSIJ-UHFFFAOYSA-N 1-[1-(3-bromo-4-methoxyphenyl)-2-piperazin-1-ylethyl]cyclopentan-1-ol Chemical compound C1=C(Br)C(OC)=CC=C1C(C1(O)CCCC1)CN1CCNCC1 BSNFRMQEINNSIJ-UHFFFAOYSA-N 0.000 claims description 2
- OBYMFFTYBMFUTN-UHFFFAOYSA-N 1-[1-(3-bromophenyl)-2-piperazin-1-ylethyl]cyclobutan-1-ol Chemical compound C1CNCCN1CC(C=1C=C(Br)C=CC=1)C1(O)CCC1 OBYMFFTYBMFUTN-UHFFFAOYSA-N 0.000 claims description 2
- HHRVKAJJFQQGMY-UHFFFAOYSA-N 1-[1-(3-bromophenyl)-2-piperazin-1-ylethyl]cycloheptan-1-ol Chemical compound C1CNCCN1CC(C=1C=C(Br)C=CC=1)C1(O)CCCCCC1 HHRVKAJJFQQGMY-UHFFFAOYSA-N 0.000 claims description 2
- QIEWQGGMPRNSTF-UHFFFAOYSA-N 1-[1-(3-bromophenyl)-2-piperazin-1-ylethyl]cyclohexan-1-ol Chemical compound C1CNCCN1CC(C=1C=C(Br)C=CC=1)C1(O)CCCCC1 QIEWQGGMPRNSTF-UHFFFAOYSA-N 0.000 claims description 2
- DHGBPKXIJTZIQH-UHFFFAOYSA-N 1-[1-(3-bromophenyl)-2-piperazin-1-ylethyl]cyclopentan-1-ol Chemical compound C1CNCCN1CC(C=1C=C(Br)C=CC=1)C1(O)CCCC1 DHGBPKXIJTZIQH-UHFFFAOYSA-N 0.000 claims description 2
- CNGLIEZZMOIJGV-UHFFFAOYSA-N 1-[1-(3-chlorophenyl)-2-(4-methylpiperazin-1-yl)ethyl]cyclobutan-1-ol Chemical compound C1CN(C)CCN1CC(C1(O)CCC1)C1=CC=CC(Cl)=C1 CNGLIEZZMOIJGV-UHFFFAOYSA-N 0.000 claims description 2
- SIMGTBMOANUZIG-NNJIEVJOSA-N 1-[1-(3-chlorophenyl)-2-[(3r)-3-methylpiperazin-1-yl]ethyl]cyclohexan-1-ol Chemical compound C1CN[C@H](C)CN1CC(C1(O)CCCCC1)C1=CC=CC(Cl)=C1 SIMGTBMOANUZIG-NNJIEVJOSA-N 0.000 claims description 2
- SIMGTBMOANUZIG-BUSXIPJBSA-N 1-[1-(3-chlorophenyl)-2-[(3s)-3-methylpiperazin-1-yl]ethyl]cyclohexan-1-ol Chemical compound C1CN[C@@H](C)CN1CC(C1(O)CCCCC1)C1=CC=CC(Cl)=C1 SIMGTBMOANUZIG-BUSXIPJBSA-N 0.000 claims description 2
- GNFBWBLHLHVEHI-UHFFFAOYSA-N 1-[1-(3-chlorophenyl)-2-piperazin-1-ylethyl]cycloheptan-1-ol Chemical compound C1CNCCN1CC(C=1C=C(Cl)C=CC=1)C1(O)CCCCCC1 GNFBWBLHLHVEHI-UHFFFAOYSA-N 0.000 claims description 2
- BDZIOTCFFYFCSB-UHFFFAOYSA-N 1-[1-(3-chlorophenyl)-2-piperazin-1-ylethyl]cyclopentan-1-ol Chemical compound C1CNCCN1CC(C=1C=C(Cl)C=CC=1)C1(O)CCCC1 BDZIOTCFFYFCSB-UHFFFAOYSA-N 0.000 claims description 2
- APZLULIMMIJDAY-UHFFFAOYSA-N 1-[1-(3-fluorophenyl)-2-(4-methylpiperazin-1-yl)ethyl]cyclobutan-1-ol Chemical compound C1CN(C)CCN1CC(C1(O)CCC1)C1=CC=CC(F)=C1 APZLULIMMIJDAY-UHFFFAOYSA-N 0.000 claims description 2
- QWUVCZDEMPCCJX-UHFFFAOYSA-N 1-[1-(3-fluorophenyl)-2-piperazin-1-ylethyl]cyclobutan-1-ol Chemical compound C1CNCCN1CC(C=1C=C(F)C=CC=1)C1(O)CCC1 QWUVCZDEMPCCJX-UHFFFAOYSA-N 0.000 claims description 2
- ZNOWPRXCOCARHQ-UHFFFAOYSA-N 1-[1-(4-bromophenyl)-2-(4-methylpiperazin-1-yl)ethyl]cyclobutan-1-ol Chemical compound C1CN(C)CCN1CC(C1(O)CCC1)C1=CC=C(Br)C=C1 ZNOWPRXCOCARHQ-UHFFFAOYSA-N 0.000 claims description 2
- WZKIGEMCGDZHTR-UHFFFAOYSA-N 1-[1-(4-bromophenyl)-2-piperazin-1-ylethyl]cyclohexan-1-ol Chemical compound C1CNCCN1CC(C=1C=CC(Br)=CC=1)C1(O)CCCCC1 WZKIGEMCGDZHTR-UHFFFAOYSA-N 0.000 claims description 2
- FGOFHUJIOVZZQE-UHFFFAOYSA-N 1-[1-(4-chlorophenyl)-2-(4-methylpiperazin-1-yl)ethyl]cyclobutan-1-ol Chemical compound C1CN(C)CCN1CC(C1(O)CCC1)C1=CC=C(Cl)C=C1 FGOFHUJIOVZZQE-UHFFFAOYSA-N 0.000 claims description 2
- UZVBARIHCIAPAS-UHFFFAOYSA-N 1-[1-(4-fluorophenyl)-2-(4-methylpiperazin-1-yl)ethyl]cyclobutan-1-ol Chemical compound C1CN(C)CCN1CC(C1(O)CCC1)C1=CC=C(F)C=C1 UZVBARIHCIAPAS-UHFFFAOYSA-N 0.000 claims description 2
- JMKKGNSMJRPWLW-UHFFFAOYSA-N 1-[1-(4-fluorophenyl)-2-piperazin-1-ylethyl]cyclobutan-1-ol Chemical compound C1CNCCN1CC(C=1C=CC(F)=CC=1)C1(O)CCC1 JMKKGNSMJRPWLW-UHFFFAOYSA-N 0.000 claims description 2
- MCGGADLCNVOIBI-UHFFFAOYSA-N 1-[2-piperazin-1-yl-1-[3-(trifluoromethyl)phenyl]ethyl]cyclobutan-1-ol Chemical compound C1CNCCN1CC(C=1C=C(C=CC=1)C(F)(F)F)C1(O)CCC1 MCGGADLCNVOIBI-UHFFFAOYSA-N 0.000 claims description 2
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Diabetes (AREA)
- Neurosurgery (AREA)
- Urology & Nephrology (AREA)
- Pain & Pain Management (AREA)
- Endocrinology (AREA)
- Cardiology (AREA)
- Psychiatry (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Heart & Thoracic Surgery (AREA)
- Emergency Medicine (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Reproductive Health (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US51154203P | 2003-10-14 | 2003-10-14 | |
| US56146904P | 2004-04-12 | 2004-04-12 | |
| US57004004P | 2004-05-11 | 2004-05-11 | |
| US10/963,458 US7531543B2 (en) | 2003-10-14 | 2004-10-12 | Phenylpiperazine cycloalkanol derivatives and methods of their use |
| PCT/US2004/033674 WO2005037808A1 (en) | 2003-10-14 | 2004-10-13 | Phenylpiperazine cycloalkanol derivatives and methods of their use |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2007508394A true JP2007508394A (ja) | 2007-04-05 |
| JP2007508394A5 JP2007508394A5 (enExample) | 2007-11-29 |
Family
ID=34468490
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006535601A Withdrawn JP2007508394A (ja) | 2003-10-14 | 2004-10-13 | フェニルピペラジンシクロアルカノール誘導体およびその使用方法 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US7531543B2 (enExample) |
| EP (1) | EP1673358A1 (enExample) |
| JP (1) | JP2007508394A (enExample) |
| AU (1) | AU2004282166A1 (enExample) |
| BR (1) | BRPI0415478A (enExample) |
| CA (1) | CA2539763A1 (enExample) |
| MX (1) | MXPA06003877A (enExample) |
| WO (1) | WO2005037808A1 (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7524846B2 (en) * | 2003-10-14 | 2009-04-28 | Wyeth | Arylalkyl- and cycloalkylalkyl-piperazine derivatives and methods of their use |
| US7414052B2 (en) * | 2004-03-30 | 2008-08-19 | Wyeth | Phenylaminopropanol derivatives and methods of their use |
| US7517899B2 (en) * | 2004-03-30 | 2009-04-14 | Wyeth | Phenylaminopropanol derivatives and methods of their use |
| WO2007067575A2 (en) * | 2005-12-05 | 2007-06-14 | Wyeth | Process for preparing substituted aryl cycloalkanol derivatives |
Family Cites Families (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2971955A (en) * | 1958-12-29 | 1961-02-14 | Abbott Lab | Cyclohexylcarbinol derivatives of piperazine |
| US3454554A (en) | 1960-10-14 | 1969-07-08 | Colgate Palmolive Co | Aminoalkyliminodibenzyl compounds |
| CS175831B1 (enExample) | 1974-12-17 | 1977-05-31 | ||
| IL56369A (en) | 1978-01-20 | 1984-05-31 | Erba Farmitalia | Alpha-phenoxybenzyl propanolamine derivatives,their preparation and pharmaceutical compositions comprising them |
| US4310524A (en) | 1980-04-11 | 1982-01-12 | Richardson-Merrell, Inc. | TCA Composition and method for rapid onset antidepressant therapy |
| PH18686A (en) | 1981-05-26 | 1985-08-29 | Merck & Co Inc | 1-(3 halo-2-pyridinyl) piperazine |
| US4535186A (en) | 1983-04-19 | 1985-08-13 | American Home Products Corporation | 2-Phenyl-2-(1-hydroxycycloalkyl or 1-hydroxycycloalk-2-enyl)ethylamine derivatives |
| ZA864772B (en) | 1985-07-02 | 1987-02-25 | Merrell Dow Pharma | Novel chemical compounds |
| CA1327795C (en) | 1987-08-14 | 1994-03-15 | Jules Freedman | Antidepressants which are aryloxy inadanamines |
| US4826844A (en) | 1987-09-30 | 1989-05-02 | American Home Products Corporation | Substituted 1-(aralkyl-piperazinoalkyl) cycloalkanols |
| ATE114467T1 (de) | 1990-06-01 | 1994-12-15 | Merrell Dow Pharma | (+)-alpha-(2,3 dimethoxyphenyl)-1-(2- (fluorophenyl)ethyl>-4-piperidinmethanol. |
| US5502047A (en) | 1993-03-22 | 1996-03-26 | Kavey; Neil B. | Treatment for insomnia |
| CZ296263B6 (cs) | 1996-03-25 | 2006-02-15 | Eli Lilly And Company | Farmaceutická kompozice pro lécení bolesti a jejípouzití |
| KR20010015918A (ko) | 1998-03-02 | 2001-02-26 | 피터 지. 스트링거 | 안면홍조를 감소시키기 위한 플루옥세틴 히드로클로라이드 |
| ES2305606T3 (es) | 1999-04-06 | 2008-11-01 | Sepracor Inc. | Succinato de o-desmetilvenlafaxina. |
| JP2003503450A (ja) | 1999-07-01 | 2003-01-28 | ファルマシア・アンド・アップジョン・カンパニー | 高選択的ノルエピネフリン再取込みインヒビターおよびその使用方法 |
| ATE369330T1 (de) | 2001-02-12 | 2007-08-15 | Wyeth Corp | O-desmethyl-venlafaxine succinat salz |
| EP1383495A1 (en) | 2001-03-29 | 2004-01-28 | Eli Lilly And Company | Duloxetine for treatment of hot flashes |
| EP1266659A1 (en) | 2001-06-11 | 2002-12-18 | Pantarhei Bioscience B.V. | Pyridoxal in combination with serotonin re-uptake inhibitor for the treatment of hot flushes |
| US20040259850A1 (en) | 2001-10-31 | 2004-12-23 | Alves Stephen E. | Method for treating or preventing symptoms of hormonal variation including hot flashes |
| US6602911B2 (en) | 2001-11-05 | 2003-08-05 | Cypress Bioscience, Inc. | Methods of treating fibromyalgia |
| PL223471B1 (pl) | 2002-03-15 | 2016-10-31 | Cypress Bioscience Inc | Kompozycja farmaceutyczna zawierająca milnacypran do stosowania w leczeniu zespołu nadwrażliwości jelita grubego |
| TW200402289A (en) | 2002-05-17 | 2004-02-16 | Wyeth Corp | Methods of treating gastrointestinary and genitourinary pain disorders |
| CA2495452A1 (en) | 2002-08-14 | 2004-02-26 | Pharmacia & Upjohn Company Llc | Use of reboxetine for the treatment of hot flashes |
| US7345096B2 (en) | 2002-10-15 | 2008-03-18 | Wyeth | Use of norepinephrine reuptake modulators for preventing and treating vasomotor symptoms |
| US20040180879A1 (en) | 2002-10-15 | 2004-09-16 | Deecher Darlene Coleman | Novel method of treating vasomotor symptoms |
| US20040152710A1 (en) | 2002-10-15 | 2004-08-05 | Deecher Darlene Coleman | Use of norepinephrine reuptake modulators for preventing and treating vasomotor symptoms |
| US7524846B2 (en) * | 2003-10-14 | 2009-04-28 | Wyeth | Arylalkyl- and cycloalkylalkyl-piperazine derivatives and methods of their use |
-
2004
- 2004-10-12 US US10/963,458 patent/US7531543B2/en not_active Expired - Fee Related
- 2004-10-13 MX MXPA06003877A patent/MXPA06003877A/es unknown
- 2004-10-13 WO PCT/US2004/033674 patent/WO2005037808A1/en not_active Ceased
- 2004-10-13 JP JP2006535601A patent/JP2007508394A/ja not_active Withdrawn
- 2004-10-13 CA CA002539763A patent/CA2539763A1/en not_active Abandoned
- 2004-10-13 EP EP04794907A patent/EP1673358A1/en not_active Withdrawn
- 2004-10-13 AU AU2004282166A patent/AU2004282166A1/en not_active Withdrawn
- 2004-10-13 BR BRPI0415478-9A patent/BRPI0415478A/pt not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| WO2005037808A1 (en) | 2005-04-28 |
| US20050143394A1 (en) | 2005-06-30 |
| US7531543B2 (en) | 2009-05-12 |
| AU2004282166A1 (en) | 2005-04-28 |
| EP1673358A1 (en) | 2006-06-28 |
| CA2539763A1 (en) | 2005-04-28 |
| BRPI0415478A (pt) | 2006-12-26 |
| MXPA06003877A (es) | 2006-07-03 |
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