CA2366660A1 - Treatment of osteoarthritis - Google Patents
Treatment of osteoarthritis Download PDFInfo
- Publication number
- CA2366660A1 CA2366660A1 CA002366660A CA2366660A CA2366660A1 CA 2366660 A1 CA2366660 A1 CA 2366660A1 CA 002366660 A CA002366660 A CA 002366660A CA 2366660 A CA2366660 A CA 2366660A CA 2366660 A1 CA2366660 A1 CA 2366660A1
- Authority
- CA
- Canada
- Prior art keywords
- compound
- formula
- cyclobutyl
- chlorophenyl
- methylbutylamine
- 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
- 201000008482 osteoarthritis Diseases 0.000 title claims abstract description 17
- 150000001875 compounds Chemical class 0.000 claims abstract description 70
- 150000003839 salts Chemical class 0.000 claims abstract description 13
- 201000005569 Gout Diseases 0.000 claims abstract description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 9
- 150000004682 monohydrates Chemical class 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 24
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 13
- WQSACWZKKZPCHN-UHFFFAOYSA-N 1-[1-(4-chlorophenyl)cyclobutyl]-3-methylbutan-1-amine Chemical compound C=1C=C(Cl)C=CC=1C1(C(N)CC(C)C)CCC1 WQSACWZKKZPCHN-UHFFFAOYSA-N 0.000 claims description 6
- UWAOJIWUVCMBAZ-UHFFFAOYSA-N [1-[1-(4-chlorophenyl)cyclobutyl]-3-methylbutyl]-dimethylazanium;chloride Chemical compound Cl.C=1C=C(Cl)C=CC=1C1(C(N(C)C)CC(C)C)CCC1 UWAOJIWUVCMBAZ-UHFFFAOYSA-N 0.000 claims description 5
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
- KFNNPQDSPLWLCX-UHFFFAOYSA-N 1-[1-(4-chlorophenyl)cyclobutyl]-n,n,3-trimethylbutan-1-amine;hydron;chloride;hydrate Chemical compound O.Cl.C=1C=C(Cl)C=CC=1C1(C(N(C)C)CC(C)C)CCC1 KFNNPQDSPLWLCX-UHFFFAOYSA-N 0.000 claims description 4
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- 239000003112 inhibitor Substances 0.000 description 7
- UNAANXDKBXWMLN-UHFFFAOYSA-N sibutramine Chemical compound C=1C=C(Cl)C=CC=1C1(C(N(C)C)CC(C)C)CCC1 UNAANXDKBXWMLN-UHFFFAOYSA-N 0.000 description 7
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- PLXKZKLXYHLWHR-UHFFFAOYSA-N 1-[1-(4-chlorophenyl)cyclobutyl]-n,3-dimethylbutan-1-amine Chemical compound C=1C=C(Cl)C=CC=1C1(C(CC(C)C)NC)CCC1 PLXKZKLXYHLWHR-UHFFFAOYSA-N 0.000 description 2
- HCYAFALTSJYZDH-UHFFFAOYSA-N Desimpramine Chemical compound C1CC2=CC=CC=C2N(CCCNC)C2=CC=CC=C21 HCYAFALTSJYZDH-UHFFFAOYSA-N 0.000 description 2
- 206010026749 Mania Diseases 0.000 description 2
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 235000019271 petrolatum Nutrition 0.000 description 2
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- PNVNVHUZROJLTJ-UHFFFAOYSA-N venlafaxine Chemical compound C1=CC(OC)=CC=C1C(CN(C)C)C1(O)CCCCC1 PNVNVHUZROJLTJ-UHFFFAOYSA-N 0.000 description 2
- QZAYGJVTTNCVMB-PZFLKRBQSA-N 3-(2-amino-1,2-ditritioethyl)-1h-indol-5-ol Chemical compound C1=C(O)C=C2C(C([3H])C(N)[3H])=CNC2=C1 QZAYGJVTTNCVMB-PZFLKRBQSA-N 0.000 description 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- UCTMLZBVNPSJHC-UHFFFAOYSA-N 5-(2-aminoethyl)cyclohexa-2,4-diene-1,2-diol Chemical compound NCCC1=CC=C(O)C(O)C1 UCTMLZBVNPSJHC-UHFFFAOYSA-N 0.000 description 1
- DEXFNLNNUZKHNO-UHFFFAOYSA-N 6-[3-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperidin-1-yl]-3-oxopropyl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1CCN(CC1)C(CCC1=CC2=C(NC(O2)=O)C=C1)=O DEXFNLNNUZKHNO-UHFFFAOYSA-N 0.000 description 1
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- 206010012735 Diarrhoea Diseases 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- 208000010201 Exanthema Diseases 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 208000002705 Glucose Intolerance Diseases 0.000 description 1
- 206010019233 Headaches Diseases 0.000 description 1
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- 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
- 208000000112 Myalgia Diseases 0.000 description 1
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 1
- 206010028813 Nausea Diseases 0.000 description 1
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- 239000004264 Petrolatum Substances 0.000 description 1
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- 206010044565 Tremor Diseases 0.000 description 1
- 206010047700 Vomiting Diseases 0.000 description 1
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000012042 active reagent Substances 0.000 description 1
- 230000036506 anxiety Effects 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 206010003549 asthenia Diseases 0.000 description 1
- 238000011914 asymmetric synthesis Methods 0.000 description 1
- 235000013871 bee wax Nutrition 0.000 description 1
- 239000012166 beeswax Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 210000005013 brain tissue Anatomy 0.000 description 1
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- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229940081734 cellulose acetate phthalate Drugs 0.000 description 1
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- 229960001760 dimethyl sulfoxide Drugs 0.000 description 1
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- 239000007884 disintegrant Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical class CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 1
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- 231100000252 nontoxic Toxicity 0.000 description 1
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- 239000003921 oil Substances 0.000 description 1
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- 239000003883 ointment base Substances 0.000 description 1
- 239000006186 oral dosage form Substances 0.000 description 1
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- 238000007911 parenteral administration Methods 0.000 description 1
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- 239000002831 pharmacologic agent Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 201000009104 prediabetes syndrome Diseases 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- -1 racemates Chemical compound 0.000 description 1
- 206010037844 rash Diseases 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 229940076279 serotonin Drugs 0.000 description 1
- 231100000872 sexual dysfunction Toxicity 0.000 description 1
- 229960003466 sibutramine hydrochloride Drugs 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
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- 229920003002 synthetic resin Polymers 0.000 description 1
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- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 230000009466 transformation Effects 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
- 208000001072 type 2 diabetes mellitus Diseases 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000001993 wax Substances 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
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
-
- 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
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
- A61K31/137—Arylalkylamines, e.g. amphetamine, epinephrine, salbutamol, ephedrine or methadone
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Emergency Medicine (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12530099P | 1999-03-19 | 1999-03-19 | |
| US60/125,300 | 1999-03-19 | ||
| PCT/US2000/007072 WO2000056306A1 (en) | 1999-03-19 | 2000-03-17 | Treatment of osteoarthritis |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2366660A1 true CA2366660A1 (en) | 2000-09-28 |
Family
ID=22419072
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002366660A Abandoned CA2366660A1 (en) | 1999-03-19 | 2000-03-17 | Treatment of osteoarthritis |
Country Status (20)
| Country | Link |
|---|---|
| EP (1) | EP1169027A4 (ja) |
| JP (2) | JP2002539248A (ja) |
| KR (1) | KR20020038567A (ja) |
| CN (1) | CN1352552A (ja) |
| AU (1) | AU773490B2 (ja) |
| BG (1) | BG105999A (ja) |
| BR (1) | BR0009081A (ja) |
| CA (1) | CA2366660A1 (ja) |
| CZ (1) | CZ20013284A3 (ja) |
| HK (1) | HK1044702A1 (ja) |
| HU (1) | HUP0200494A2 (ja) |
| IL (1) | IL145238A0 (ja) |
| MX (1) | MXPA01009461A (ja) |
| NO (1) | NO20014477L (ja) |
| NZ (1) | NZ514016A (ja) |
| PL (1) | PL365463A1 (ja) |
| SK (1) | SK13342001A3 (ja) |
| TR (1) | TR200102699T2 (ja) |
| WO (1) | WO2000056306A1 (ja) |
| ZA (1) | ZA200107682B (ja) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6974838B2 (en) | 1998-08-24 | 2005-12-13 | Sepracor Inc. | Methods of treating or preventing pain using sibutramine metabolites |
| US6476078B2 (en) | 1999-08-11 | 2002-11-05 | Sepracor, Inc. | Methods of using sibutramine metabolites in combination with a phosphodiesterase inhibitor to treat sexual dysfunction |
| US6399826B1 (en) | 1999-08-11 | 2002-06-04 | Sepracor Inc. | Salts of sibutramine metabolites, methods of making sibutramine metabolites and intermediates useful in the same, and methods of treating pain |
| US6610887B2 (en) | 2001-04-13 | 2003-08-26 | Sepracor Inc. | Methods of preparing didesmethylsibutramine and other sibutramine derivatives |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA821577B (en) * | 1981-04-06 | 1983-03-30 | Boots Co Plc | Therapeutic agents |
| ZA836848B (en) * | 1982-09-30 | 1984-05-30 | Boots Co Plc | Therapeutic agents |
| GB8531071D0 (en) * | 1985-12-17 | 1986-01-29 | Boots Co Plc | Therapeutic compound |
| JP2675573B2 (ja) * | 1988-03-31 | 1997-11-12 | 科研製薬株式会社 | 脳機能改善剤 |
| IE61928B1 (en) * | 1988-11-29 | 1994-11-30 | Boots Co Plc | Treatment of obesity |
| EP0647134A4 (en) * | 1992-06-23 | 1997-07-30 | Sepracor Inc | METHODS AND COMPOSITIONS USED TO TREAT DEPRESSION AND OTHER CONDITIONS WITH OPTICALLY PURE SIBUTRAMINE (-). |
| AU4542993A (en) * | 1992-06-23 | 1994-01-24 | Sepracor, Inc. | Methods and compositions for treating depression and other disorders using optically pure (+) sibutramine |
| JP3862295B2 (ja) * | 1993-09-30 | 2006-12-27 | 独立行政法人理化学研究所 | 抗肥満剤 |
| US5459164A (en) * | 1994-02-03 | 1995-10-17 | Boots Pharmaceuticals, Inc. | Medical treatment |
| JPH10501238A (ja) * | 1994-06-01 | 1998-02-03 | アリス ファーマシューティカル コーポレイション | 肥満細胞媒介症状を治療するための組成物及び方法 |
| GB9619962D0 (en) * | 1996-09-25 | 1996-11-13 | Knoll Ag | Medical treatment |
| MA24500A1 (fr) * | 1997-03-21 | 1998-10-01 | Lg Life Sciences Ltd | Derive du sel d'acide carboxylique de naphthyridine . |
-
2000
- 2000-03-17 MX MXPA01009461A patent/MXPA01009461A/es unknown
- 2000-03-17 CN CN00807529A patent/CN1352552A/zh active Pending
- 2000-03-17 WO PCT/US2000/007072 patent/WO2000056306A1/en not_active Application Discontinuation
- 2000-03-17 CA CA002366660A patent/CA2366660A1/en not_active Abandoned
- 2000-03-17 SK SK1334-2001A patent/SK13342001A3/sk unknown
- 2000-03-17 NZ NZ514016A patent/NZ514016A/xx not_active Application Discontinuation
- 2000-03-17 JP JP2000606211A patent/JP2002539248A/ja active Pending
- 2000-03-17 HU HU0200494A patent/HUP0200494A2/hu unknown
- 2000-03-17 AU AU38932/00A patent/AU773490B2/en not_active Ceased
- 2000-03-17 EP EP00918058A patent/EP1169027A4/en not_active Withdrawn
- 2000-03-17 IL IL14523800A patent/IL145238A0/xx unknown
- 2000-03-17 CZ CZ20013284A patent/CZ20013284A3/cs unknown
- 2000-03-17 BR BR0009081-6A patent/BR0009081A/pt not_active Application Discontinuation
- 2000-03-17 KR KR1020017011852A patent/KR20020038567A/ko not_active Application Discontinuation
- 2000-03-17 PL PL00365463A patent/PL365463A1/xx unknown
- 2000-03-17 TR TR2001/02699T patent/TR200102699T2/xx unknown
-
2001
- 2001-09-14 NO NO20014477A patent/NO20014477L/no unknown
- 2001-09-18 ZA ZA200107682A patent/ZA200107682B/en unknown
- 2001-10-10 BG BG105999A patent/BG105999A/xx unknown
-
2002
- 2002-06-20 HK HK02104603.9A patent/HK1044702A1/zh unknown
-
2011
- 2011-10-04 JP JP2011220221A patent/JP2012051904A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| BG105999A (en) | 2002-06-28 |
| MXPA01009461A (es) | 2004-03-19 |
| NO20014477L (no) | 2001-11-01 |
| JP2012051904A (ja) | 2012-03-15 |
| NZ514016A (en) | 2001-09-28 |
| JP2002539248A (ja) | 2002-11-19 |
| SK13342001A3 (sk) | 2002-04-04 |
| AU773490B2 (en) | 2004-05-27 |
| KR20020038567A (ko) | 2002-05-23 |
| EP1169027A4 (en) | 2004-10-20 |
| BR0009081A (pt) | 2003-03-05 |
| HUP0200494A2 (en) | 2002-08-28 |
| WO2000056306A1 (en) | 2000-09-28 |
| HK1044702A1 (zh) | 2002-11-01 |
| NO20014477D0 (no) | 2001-09-14 |
| CZ20013284A3 (cs) | 2002-10-16 |
| IL145238A0 (en) | 2002-06-30 |
| TR200102699T2 (tr) | 2002-03-21 |
| CN1352552A (zh) | 2002-06-05 |
| PL365463A1 (en) | 2005-01-10 |
| ZA200107682B (en) | 2003-06-18 |
| EP1169027A1 (en) | 2002-01-09 |
| AU3893200A (en) | 2000-10-09 |
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| EEER | Examination request | ||
| FZDE | Discontinued |