HUP0200494A2 - Use of-n,n-dimethyl-1-[1-(4 chlorophenyl)cyclobutyl]-3-metilbutilamine for treatment of osteoarthritis - Google Patents

Use of-n,n-dimethyl-1-[1-(4 chlorophenyl)cyclobutyl]-3-metilbutilamine for treatment of osteoarthritis Download PDF

Info

Publication number: HUP0200494A2
Authority: HU; Hungary
Prior art keywords: cyclobutyl; chlorophenyl; compound; general formula; process according
Prior art date: 1999-03-19

Application number

HU0200494A

Other languages

English (en)

Hungarian (hu)

Inventor

Carl M Mendel

Timothy B Seaton

Steve P Weinstein

Original Assignee

Knoll Gmbh

Priority date (The priority date 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 date listed.)

1999-03-19

Filing date

2000-03-17

Publication date

2002-08-28

2000-03-17 Application filed by Knoll Gmbh filed Critical Knoll Gmbh

2002-08-28 Publication of HUP0200494A2 publication Critical patent/HUP0200494A2/hu

Links

201000008482 osteoarthritis Diseases 0.000 title claims description 14
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 title claims description 3
150000001875 compounds Chemical class 0.000 claims description 47
238000000034 method Methods 0.000 claims description 15
150000003839 salts Chemical class 0.000 claims description 12
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 claims description 12
201000005569 Gout Diseases 0.000 claims description 11
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
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 7
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 claims description 7
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
238000002360 preparation method Methods 0.000 claims description 7
239000008194 pharmaceutical composition Substances 0.000 claims description 6
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 5
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 5
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 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
239000003085 diluting agent Substances 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
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HCYAFALTSJYZDH-UHFFFAOYSA-N Desimpramine Chemical compound C1CC2=CC=CC=C2N(CCCNC)C2=CC=CC=C21 HCYAFALTSJYZDH-UHFFFAOYSA-N 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
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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
SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-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
208000006820 Arthralgia Diseases 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
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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
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VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical group O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
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206010044565 Tremor Diseases 0.000 description 1
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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
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239000001506 calcium phosphate Substances 0.000 description 1
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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
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POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical class CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 1
VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 1
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210000004400 mucous membrane Anatomy 0.000 description 1
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229960002748 norepinephrine Drugs 0.000 description 1
SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 1
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239000002831 pharmacologic agent Substances 0.000 description 1
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239000003380 propellant Substances 0.000 description 1
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238000000926 separation method Methods 0.000 description 1
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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
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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
- A61K31/13—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)

HU0200494A 1999-03-19 2000-03-17 Use of-n,n-dimethyl-1-[1-(4 chlorophenyl)cyclobutyl]-3-metilbutilamine for treatment of osteoarthritis HUP0200494A2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US12530099P	1999-03-19	1999-03-19

Publications (1)

Publication Number	Publication Date
HUP0200494A2 true HUP0200494A2 (en)	2002-08-28

Family

ID=22419072

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
HU0200494A HUP0200494A2 (en)	1999-03-19	2000-03-17	Use of-n,n-dimethyl-1-[1-(4 chlorophenyl)cyclobutyl]-3-metilbutilamine for treatment of osteoarthritis

Country Status (20)

Country	Link
EP (1)	EP1169027A4 (pl)
JP (2)	JP2002539248A (pl)
KR (1)	KR20020038567A (pl)
CN (1)	CN1352552A (pl)
AU (1)	AU773490B2 (pl)
BG (1)	BG105999A (pl)
BR (1)	BR0009081A (pl)
CA (1)	CA2366660A1 (pl)
CZ (1)	CZ20013284A3 (pl)
HK (1)	HK1044702A1 (pl)
HU (1)	HUP0200494A2 (pl)
IL (1)	IL145238A0 (pl)
MX (1)	MXPA01009461A (pl)
NO (1)	NO20014477L (pl)
NZ (1)	NZ514016A (pl)
PL (1)	PL365463A1 (pl)
SK (1)	SK13342001A3 (pl)
TR (1)	TR200102699T2 (pl)
WO (1)	WO2000056306A1 (pl)
ZA (1)	ZA200107682B (pl)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
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
US6974838B2 (en)	1998-08-24	2005-12-13	Sepracor Inc.	Methods of treating or preventing pain using sibutramine metabolites
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
WO2002083631A1 (en)	2001-04-13	2002-10-24	Sepracor Inc.	Methods of preparing didesmethylsibutramine and other sibutramine derivatives

Family Cites Families (12)

* Cited by examiner, † Cited by third party
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
CA2138998A1 (en) *	1992-06-23	1994-01-06	James W. Young	Methods and compositions for treating depression and other disorders using optically pure(-) sibutramine
CA2139000A1 (en) *	1992-06-23	1994-01-06	James W. Young	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
AU2764495A (en) *	1994-06-01	1995-12-21	Arris Pharmaceutical Corporation	Compositions and methods for treating mast-cell mediated conditions
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 PL PL00365463A patent/PL365463A1/pl unknown
- 2000-03-17 BR BR0009081-6A patent/BR0009081A/pt not_active Application Discontinuation
- 2000-03-17 CN CN00807529A patent/CN1352552A/zh active Pending
- 2000-03-17 NZ NZ514016A patent/NZ514016A/xx not_active Application Discontinuation
- 2000-03-17 AU AU38932/00A patent/AU773490B2/en not_active Ceased
- 2000-03-17 JP JP2000606211A patent/JP2002539248A/ja active Pending
- 2000-03-17 IL IL14523800A patent/IL145238A0/xx unknown
- 2000-03-17 CZ CZ20013284A patent/CZ20013284A3/cs unknown
- 2000-03-17 KR KR1020017011852A patent/KR20020038567A/ko not_active Ceased
- 2000-03-17 SK SK1334-2001A patent/SK13342001A3/sk unknown
- 2000-03-17 TR TR2001/02699T patent/TR200102699T2/xx unknown
- 2000-03-17 HU HU0200494A patent/HUP0200494A2/hu unknown
- 2000-03-17 MX MXPA01009461A patent/MXPA01009461A/es unknown
- 2000-03-17 HK HK02104603.9A patent/HK1044702A1/zh unknown
- 2000-03-17 WO PCT/US2000/007072 patent/WO2000056306A1/en not_active Ceased
- 2000-03-17 EP EP00918058A patent/EP1169027A4/en not_active Withdrawn
- 2000-03-17 CA CA002366660A patent/CA2366660A1/en not_active Abandoned
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
2011
- 2011-10-04 JP JP2011220221A patent/JP2012051904A/ja active Pending

Also Published As

Publication number	Publication date
JP2012051904A (ja)	2012-03-15
AU773490B2 (en)	2004-05-27
MXPA01009461A (es)	2004-03-19
IL145238A0 (en)	2002-06-30
PL365463A1 (pl)	2005-01-10
NO20014477D0 (no)	2001-09-14
JP2002539248A (ja)	2002-11-19
KR20020038567A (ko)	2002-05-23
CA2366660A1 (en)	2000-09-28
SK13342001A3 (sk)	2002-04-04
EP1169027A4 (en)	2004-10-20
NZ514016A (en)	2001-09-28
AU3893200A (en)	2000-10-09
NO20014477L (no)	2001-11-01
ZA200107682B (en)	2003-06-18
BG105999A (en)	2002-06-28
CZ20013284A3 (cs)	2002-10-16
HK1044702A1 (zh)	2002-11-01
TR200102699T2 (tr)	2002-03-21
BR0009081A (pt)	2003-03-05
EP1169027A1 (en)	2002-01-09
CN1352552A (zh)	2002-06-05
WO2000056306A1 (en)	2000-09-28

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HUP0200497A2 (en)	2002-08-28	Use of n,n-dimethyl-1-[1-(4chlorophenyl)cyclobutyl]-3-methylbutylamine for treatment of certain cancers associated with weight gain
US6433020B1 (en)	2002-08-13	Treatment of cardiovascular disease
HUP0200500A2 (en)	2002-08-28	Use of n,n-dimethyl-1-[1-(4chlorophenyl)cyclobutyl]-3-methylbutylamine for aiding weight loss after pregnancy
US20020132856A1 (en)	2002-09-19	Treatment of premenstrual syndrome
JP2002539249A (ja)	2002-11-19	裂孔ヘルニアの治療