AU2004282166A1 - Phenylpiperazine cycloalkanol derivatives and methods of their use - Google Patents
Phenylpiperazine cycloalkanol derivatives and methods of their use Download PDFInfo
- Publication number
- AU2004282166A1 AU2004282166A1 AU2004282166A AU2004282166A AU2004282166A1 AU 2004282166 A1 AU2004282166 A1 AU 2004282166A1 AU 2004282166 A AU2004282166 A AU 2004282166A AU 2004282166 A AU2004282166 A AU 2004282166A AU 2004282166 A1 AU2004282166 A1 AU 2004282166A1
- Authority
- AU
- Australia
- 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- Withdrawn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 description 60
- YZTJYBJCZXZGCT-UHFFFAOYSA-N phenylpiperazine Chemical compound C1CNCCN1C1=CC=CC=C1 YZTJYBJCZXZGCT-UHFFFAOYSA-N 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims description 115
- -1 CF 3 Chemical group 0.000 claims description 58
- 208000002193 Pain Diseases 0.000 claims description 54
- 230000036407 pain Effects 0.000 claims description 49
- 150000003839 salts Chemical class 0.000 claims description 41
- 208000024891 symptom Diseases 0.000 claims description 36
- 125000004432 carbon atom Chemical group C* 0.000 claims description 28
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 28
- 208000035475 disorder Diseases 0.000 claims description 27
- 230000001457 vasomotor Effects 0.000 claims description 27
- 239000000203 mixture Substances 0.000 claims description 26
- 206010060800 Hot flush Diseases 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- 201000001880 Sexual dysfunction Diseases 0.000 claims description 15
- 231100000872 sexual dysfunction Toxicity 0.000 claims description 15
- 125000000623 heterocyclic group Chemical group 0.000 claims description 14
- 206010066218 Stress Urinary Incontinence Diseases 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 206010008874 Chronic Fatigue Syndrome Diseases 0.000 claims description 9
- 208000000921 Urge Urinary Incontinence Diseases 0.000 claims description 9
- 230000001668 ameliorated effect Effects 0.000 claims description 9
- 230000002496 gastric effect Effects 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 230000000407 monoamine reuptake Effects 0.000 claims description 9
- 208000029766 myalgic encephalomeyelitis/chronic fatigue syndrome Diseases 0.000 claims description 9
- 208000011580 syndromic disease Diseases 0.000 claims description 9
- 208000032131 Diabetic Neuropathies Diseases 0.000 claims description 8
- 208000001640 Fibromyalgia Diseases 0.000 claims description 8
- 208000012902 Nervous system disease Diseases 0.000 claims description 8
- 150000001721 carbon Chemical group 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
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- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 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 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
- 125000004423 acyloxy group Chemical group 0.000 claims description 4
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
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- 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 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
- 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 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
- 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 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
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- 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
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- 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
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- 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
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- SZOBXZLRTBAKOP-UHFFFAOYSA-N tert-butyl 4-[2-(3-bromophenyl)-2-(1-hydroxycyclooctyl)acetyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1C(=O)C(C1(O)CCCCCCC1)C1=CC=CC(Br)=C1 SZOBXZLRTBAKOP-UHFFFAOYSA-N 0.000 description 1
- JQGWYFQWYZGKSM-UHFFFAOYSA-N tert-butyl 4-[2-(3-bromophenyl)-2-(1-hydroxycyclopentyl)acetyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1C(=O)C(C1(O)CCCC1)C1=CC=CC(Br)=C1 JQGWYFQWYZGKSM-UHFFFAOYSA-N 0.000 description 1
- KJVNOVXSGSAAPV-UHFFFAOYSA-N tert-butyl 4-[2-(3-chlorophenyl)-2-(1-hydroxycyclobutyl)acetyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1C(=O)C(C1(O)CCC1)C1=CC=CC(Cl)=C1 KJVNOVXSGSAAPV-UHFFFAOYSA-N 0.000 description 1
- UGADTZVGCAIYKB-UHFFFAOYSA-N tert-butyl 4-[2-(3-chlorophenyl)-2-(1-hydroxycycloheptyl)acetyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1C(=O)C(C1(O)CCCCCC1)C1=CC=CC(Cl)=C1 UGADTZVGCAIYKB-UHFFFAOYSA-N 0.000 description 1
- MMZNOOMGULOSHB-UHFFFAOYSA-N tert-butyl 4-[2-(3-chlorophenyl)-2-(1-hydroxycyclooctyl)acetyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1C(=O)C(C1(O)CCCCCCC1)C1=CC=CC(Cl)=C1 MMZNOOMGULOSHB-UHFFFAOYSA-N 0.000 description 1
- FVXCBWJOXSBSLJ-UHFFFAOYSA-N tert-butyl 4-[2-(3-chlorophenyl)-2-(1-hydroxycyclopentyl)acetyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1C(=O)C(C1(O)CCCC1)C1=CC=CC(Cl)=C1 FVXCBWJOXSBSLJ-UHFFFAOYSA-N 0.000 description 1
- WRSLVLVJYCPDNV-UHFFFAOYSA-N tert-butyl 4-[2-(3-fluorophenyl)-2-(1-hydroxycyclobutyl)acetyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1C(=O)C(C1(O)CCC1)C1=CC=CC(F)=C1 WRSLVLVJYCPDNV-UHFFFAOYSA-N 0.000 description 1
- ULSQPRDJRAOVKW-UHFFFAOYSA-N tert-butyl 4-[2-(3-fluorophenyl)-2-(1-hydroxycyclohexyl)acetyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1C(=O)C(C1(O)CCCCC1)C1=CC=CC(F)=C1 ULSQPRDJRAOVKW-UHFFFAOYSA-N 0.000 description 1
- YAMMQKCNVCWYRS-UHFFFAOYSA-N tert-butyl 4-[2-(4-bromophenyl)-2-(1-hydroxycyclobutyl)acetyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1C(=O)C(C1(O)CCC1)C1=CC=C(Br)C=C1 YAMMQKCNVCWYRS-UHFFFAOYSA-N 0.000 description 1
- LPZIKBVTGDEXCT-UHFFFAOYSA-N tert-butyl 4-[2-(4-bromophenyl)-2-(1-hydroxycyclohexyl)ethyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1CC(C1(O)CCCCC1)C1=CC=C(Br)C=C1 LPZIKBVTGDEXCT-UHFFFAOYSA-N 0.000 description 1
- QORPEGKTKHVBOV-UHFFFAOYSA-N tert-butyl 4-[2-(4-chlorophenyl)-2-(1-hydroxycyclohexyl)acetyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1C(=O)C(C1(O)CCCCC1)C1=CC=C(Cl)C=C1 QORPEGKTKHVBOV-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 description 1
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 208000012720 thalamic disease Diseases 0.000 description 1
- 230000000542 thalamic effect Effects 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000004797 therapeutic response Effects 0.000 description 1
- 125000004627 thianthrenyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3SC12)* 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000003053 toxin Substances 0.000 description 1
- 231100000765 toxin Toxicity 0.000 description 1
- 108700012359 toxins Proteins 0.000 description 1
- 230000032258 transport Effects 0.000 description 1
- 230000000472 traumatic effect Effects 0.000 description 1
- 238000011269 treatment regimen Methods 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 206010046494 urge incontinence Diseases 0.000 description 1
- 230000024883 vasodilation Effects 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
- 230000008673 vomiting Effects 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- 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
-
- 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
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- 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
Landscapes
- 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 (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US51154203P | 2003-10-14 | 2003-10-14 | |
| US60/511,542 | 2003-10-14 | ||
| US56146904P | 2004-04-12 | 2004-04-12 | |
| US60/561,469 | 2004-04-12 | ||
| US57004004P | 2004-05-11 | 2004-05-11 | |
| US60/570,040 | 2004-05-11 | ||
| US10/963,458 US7531543B2 (en) | 2003-10-14 | 2004-10-12 | Phenylpiperazine cycloalkanol derivatives and methods of their use |
| US10/963,458 | 2004-10-12 | ||
| PCT/US2004/033674 WO2005037808A1 (en) | 2003-10-14 | 2004-10-13 | Phenylpiperazine cycloalkanol derivatives and methods of their use |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AU2004282166A1 true AU2004282166A1 (en) | 2005-04-28 |
Family
ID=34468490
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2004282166A Withdrawn AU2004282166A1 (en) | 2003-10-14 | 2004-10-13 | Phenylpiperazine cycloalkanol derivatives and methods of their use |
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 |
| EP1673358A1 (en) | 2006-06-28 |
| JP2007508394A (ja) | 2007-04-05 |
| CA2539763A1 (en) | 2005-04-28 |
| BRPI0415478A (pt) | 2006-12-26 |
| MXPA06003877A (es) | 2006-07-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK12 | Application lapsed section 141(1)/reg 8.3(2) - applicant filed a written notice of withdrawal |