OA12659A - Urea-compounds active as vanilloid receptor antagonists for the treatment of pain. - Google Patents

Urea-compounds active as vanilloid receptor antagonists for the treatment of pain. Download PDF

Info

Publication number: OA12659A
Authority: OA; OAPI
Prior art keywords: urea; pyrrolidin; methylphenyl; bromophenyl; dichlorophenyl
Prior art date: 2001-09-13

Application number

OA1200400070A

Other languages

English (en)

Inventor

Harshad Kantilal Rami

Mervyn Thompson

Paul Adrian Wyman

Original Assignee

Smithkline Beecham Plc

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.)

2001-09-13

Filing date

2002-09-13

Publication date

2006-06-19

2001-09-13 Priority claimed from GB0122156A external-priority patent/GB0122156D0/en

2001-12-20 Priority claimed from GB0130503A external-priority patent/GB0130503D0/en

2001-12-20 Priority claimed from GB0130505A external-priority patent/GB0130505D0/en

2001-12-20 Priority claimed from GB0130547A external-priority patent/GB0130547D0/en

2002-09-13 Application filed by Smithkline Beecham Plc filed Critical Smithkline Beecham Plc

2006-06-19 Publication of OA12659A publication Critical patent/OA12659A/en

Links

208000002193 Pain Diseases 0.000 title description 12
238000011282 treatment Methods 0.000 title description 12
239000000085 vanilloid receptor antagonist Substances 0.000 title description 9
150000001875 compounds Chemical class 0.000 claims abstract description 116
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 179
239000004202 carbamide Substances 0.000 claims description 100
125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 45
-1 polymethylene Chain Polymers 0.000 claims description 45
125000000217 alkyl group Chemical group 0.000 claims description 36
125000003545 alkoxy group Chemical group 0.000 claims description 20
125000003118 aryl group Chemical group 0.000 claims description 13
125000003710 aryl alkyl group Chemical group 0.000 claims description 6
125000000753 cycloalkyl group Chemical group 0.000 claims description 6
229910052739 hydrogen Inorganic materials 0.000 claims description 6
GJKCYSMZYSMYRW-UHFFFAOYSA-N 1-(4-methoxyphenyl)-3-(1-phenylpyrrolidin-3-yl)urea Chemical compound C1=CC(OC)=CC=C1NC(=O)NC1CN(C=2C=CC=CC=2)CC1 GJKCYSMZYSMYRW-UHFFFAOYSA-N 0.000 claims description 4
125000004429 atom Chemical group 0.000 claims description 4
150000003976 azacycloalkanes Chemical group 0.000 claims description 4
125000005842 heteroatom Chemical group 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
241000080590 Niso Species 0.000 claims description 3
125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 2
125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 2
150000003839 salts Chemical class 0.000 abstract description 13
229910052698 phosphorus Inorganic materials 0.000 abstract description 7
239000000203 mixture Substances 0.000 abstract description 4
239000008194 pharmaceutical composition Substances 0.000 abstract description 4
239000003814 drug Substances 0.000 abstract description 3
238000004519 manufacturing process Methods 0.000 abstract description 2
239000012453 solvate Substances 0.000 abstract 1
238000000034 method Methods 0.000 description 48
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 42
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 34
239000000243 solution Substances 0.000 description 29
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 25
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
239000007787 solid Substances 0.000 description 21
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 18
238000006243 chemical reaction Methods 0.000 description 14
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235000019439 ethyl acetate Nutrition 0.000 description 14
125000005843 halogen group Chemical group 0.000 description 14
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 13
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239000002253 acid Substances 0.000 description 11
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 11
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 11
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CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
125000004093 cyano group Chemical group *C#N 0.000 description 10
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 10
208000035475 disorder Diseases 0.000 description 9
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YKPUWZUDDOIDPM-SOFGYWHQSA-N capsaicin Chemical compound COC1=CC(CNC(=O)CCCC\C=C\C(C)C)=CC=C1O YKPUWZUDDOIDPM-SOFGYWHQSA-N 0.000 description 8
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125000001153 fluoro group Chemical group F* 0.000 description 7
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125000001309 chloro group Chemical group Cl* 0.000 description 6
229960004132 diethyl ether Drugs 0.000 description 6
150000002148 esters Chemical class 0.000 description 6
125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 6
125000001624 naphthyl group Chemical group 0.000 description 6
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 6
229910000027 potassium carbonate Inorganic materials 0.000 description 6
229940093956 potassium carbonate Drugs 0.000 description 6
235000011181 potassium carbonates Nutrition 0.000 description 6
FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 6
239000000725 suspension Substances 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 5
125000001246 bromo group Chemical group Br* 0.000 description 5
238000004587 chromatography analysis Methods 0.000 description 5
239000012043 crude product Substances 0.000 description 5
230000000694 effects Effects 0.000 description 5
239000005457 ice water Substances 0.000 description 5
229910052943 magnesium sulfate Inorganic materials 0.000 description 5
235000019341 magnesium sulphate Nutrition 0.000 description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
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239000005557 antagonist Substances 0.000 description 4
239000011575 calcium Substances 0.000 description 4
229910052791 calcium Inorganic materials 0.000 description 4
125000004432 carbon atom Chemical group C* 0.000 description 4
229910052760 oxygen Inorganic materials 0.000 description 4
239000000047 product Substances 0.000 description 4
238000011321 prophylaxis Methods 0.000 description 4
125000004076 pyridyl group Chemical group 0.000 description 4
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 4
235000011121 sodium hydroxide Nutrition 0.000 description 4
229940083608 sodium hydroxide Drugs 0.000 description 4
229910052717 sulfur Inorganic materials 0.000 description 4
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JFZJMSDDOOAOIV-UHFFFAOYSA-N 2-chloro-5-(trifluoromethyl)pyridine Chemical compound FC(F)(F)C1=CC=C(Cl)N=C1 JFZJMSDDOOAOIV-UHFFFAOYSA-N 0.000 description 3
DTVYNUOOZIKEEX-UHFFFAOYSA-N 5-aminoisoquinoline Chemical compound N1=CC=C2C(N)=CC=CC2=C1 DTVYNUOOZIKEEX-UHFFFAOYSA-N 0.000 description 3
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ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 3
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229910052799 carbon Inorganic materials 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
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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 description 2
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
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- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
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- A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
- A—HUMAN NECESSITIES
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- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
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Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Chemical Kinetics & Catalysis (AREA)
Veterinary Medicine (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Public Health (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Pulmonology (AREA)
Pain & Pain Management (AREA)
Dermatology (AREA)
Heart & Thoracic Surgery (AREA)
Hospice & Palliative Care (AREA)
Diabetes (AREA)
Cardiology (AREA)
Urology & Nephrology (AREA)
Hematology (AREA)
Psychiatry (AREA)
Rheumatology (AREA)
Vascular Medicine (AREA)
Otolaryngology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Plural Heterocyclic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Hydrogenated Pyridines (AREA)

OA1200400070A 2001-09-13 2002-09-13 Urea-compounds active as vanilloid receptor antagonists for the treatment of pain. OA12659A (en)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
GB0122156A GB0122156D0 (en)	2001-09-13	2001-09-13	Novel compounds
GB0130503A GB0130503D0 (en)	2001-12-20	2001-12-20	Novel compounds
GB0130505A GB0130505D0 (en)	2001-12-20	2001-12-20	Novel compounds
GB0130547A GB0130547D0 (en)	2001-12-20	2001-12-20	Novel compounds

Publications (1)

Publication Number	Publication Date
OA12659A true OA12659A (en)	2006-06-19

Family

ID=27447989

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
OA1200400070A OA12659A (en)	2001-09-13	2002-09-13	Urea-compounds active as vanilloid receptor antagonists for the treatment of pain.

Country Status (31)

Country	Link
US (1)	US8063078B2 (ru)
EP (3)	EP1425277B8 (ru)
JP (2)	JP4463552B2 (ru)
KR (3)	KR101063679B1 (ru)
CN (1)	CN1247568C (ru)
AP (1)	AP1818A (ru)
AR (1)	AR038786A1 (ru)
AT (1)	ATE420083T1 (ru)
AU (1)	AU2002329397B2 (ru)
BR (1)	BR0212468A (ru)
CA (1)	CA2458632C (ru)
CY (1)	CY1109449T1 (ru)
DE (1)	DE60230773D1 (ru)
DK (1)	DK1425277T3 (ru)
EA (1)	EA007731B1 (ru)
ES (1)	ES2316607T3 (ru)
HU (1)	HUP0401923A3 (ru)
IL (2)	IL160755A0 (ru)
MA (1)	MA26216A1 (ru)
MX (1)	MXPA04002379A (ru)
MY (1)	MY138086A (ru)
NO (3)	NO327009B1 (ru)
NZ (1)	NZ531137A (ru)
OA (1)	OA12659A (ru)
PE (1)	PE20030417A1 (ru)
PL (1)	PL213639B1 (ru)
PT (1)	PT1425277E (ru)
SI (1)	SI1425277T1 (ru)
TW (1)	TWI283665B (ru)
UY (1)	UY27446A1 (ru)
WO (1)	WO2003022809A2 (ru)

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2002
- 2002-09-11 PE PE2002000895A patent/PE20030417A1/es not_active Application Discontinuation
- 2002-09-11 MY MYPI20023391A patent/MY138086A/en unknown
- 2002-09-11 TW TW091120671A patent/TWI283665B/zh not_active IP Right Cessation
- 2002-09-12 UY UY27446A patent/UY27446A1/es not_active Application Discontinuation
- 2002-09-12 AR ARP020103454A patent/AR038786A1/es active IP Right Grant
- 2002-09-13 KR KR1020047003680A patent/KR101063679B1/ko not_active Expired - Fee Related
- 2002-09-13 BR BR0212468-8A patent/BR0212468A/pt not_active IP Right Cessation
- 2002-09-13 KR KR1020107014626A patent/KR20100082390A/ko not_active Ceased
- 2002-09-13 KR KR1020097003812A patent/KR100955967B1/ko not_active Expired - Fee Related
- 2002-09-13 EP EP02765023A patent/EP1425277B8/en not_active Expired - Lifetime
- 2002-09-13 AP APAP/P/2004/002982A patent/AP1818A/en active
- 2002-09-13 WO PCT/GB2002/004206 patent/WO2003022809A2/en not_active Ceased
- 2002-09-13 MX MXPA04002379A patent/MXPA04002379A/es active IP Right Grant
- 2002-09-13 HU HU0401923A patent/HUP0401923A3/hu unknown
- 2002-09-13 ES ES02765023T patent/ES2316607T3/es not_active Expired - Lifetime
- 2002-09-13 DK DK02765023T patent/DK1425277T3/da active
- 2002-09-13 CA CA2458632A patent/CA2458632C/en not_active Expired - Fee Related
- 2002-09-13 EA EA200400432A patent/EA007731B1/ru not_active IP Right Cessation
- 2002-09-13 EP EP08172882A patent/EP2036902A3/en not_active Withdrawn
- 2002-09-13 PT PT02765023T patent/PT1425277E/pt unknown
- 2002-09-13 EP EP10179466A patent/EP2298757A3/en not_active Withdrawn
- 2002-09-13 SI SI200230792T patent/SI1425277T1/sl unknown
- 2002-09-13 US US10/489,277 patent/US8063078B2/en not_active Expired - Fee Related
- 2002-09-13 AT AT02765023T patent/ATE420083T1/de active
- 2002-09-13 AU AU2002329397A patent/AU2002329397B2/en not_active Ceased
- 2002-09-13 DE DE60230773T patent/DE60230773D1/de not_active Expired - Lifetime
- 2002-09-13 IL IL16075502A patent/IL160755A0/xx unknown
- 2002-09-13 PL PL369026A patent/PL213639B1/pl not_active IP Right Cessation
- 2002-09-13 NZ NZ531137A patent/NZ531137A/en not_active IP Right Cessation
- 2002-09-13 OA OA1200400070A patent/OA12659A/en unknown
- 2002-09-13 JP JP2003526885A patent/JP4463552B2/ja not_active Expired - Fee Related
- 2002-09-13 CN CNB028177177A patent/CN1247568C/zh not_active Expired - Fee Related
2004
- 2004-03-04 IL IL160755A patent/IL160755A/en not_active IP Right Cessation
- 2004-03-10 NO NO20041003A patent/NO327009B1/no not_active IP Right Cessation
- 2004-03-12 MA MA27573A patent/MA26216A1/fr unknown
2008
- 2008-12-04 NO NO20085077A patent/NO20085077L/no not_active Application Discontinuation
- 2008-12-04 NO NO20085078A patent/NO20085078L/no unknown
2009
- 2009-03-19 CY CY20091100306T patent/CY1109449T1/el unknown
- 2009-12-08 JP JP2009278584A patent/JP2010100632A/ja active Pending

Also Published As

Publication number	Publication date
NO20041003L (no)	2004-06-04
UY27446A1 (es)	2003-04-30
WO2003022809A3 (en)	2003-07-17
ATE420083T1 (de)	2009-01-15
US8063078B2 (en)	2011-11-22
JP4463552B2 (ja)	2010-05-19
AR038786A1 (es)	2005-01-26
AP1818A (en)	2008-01-07
EP1425277B1 (en)	2009-01-07
HUP0401923A3 (en)	2012-09-28
MA26216A1 (fr)	2004-07-01
CN1247568C (zh)	2006-03-29
EP1425277B8 (en)	2009-04-01
BR0212468A (pt)	2004-10-19
SI1425277T1 (sl)	2009-04-30
JP2010100632A (ja)	2010-05-06
JP2005504074A (ja)	2005-02-10
DE60230773D1 (de)	2009-02-26
AU2002329397B2 (en)	2006-04-27
NZ531137A (en)	2006-08-31
EP2036902A3 (en)	2009-05-06
NO20085077L (no)	2004-06-04
EA007731B1 (ru)	2006-12-29
NO327009B1 (no)	2009-04-06
PL213639B1 (pl)	2013-04-30
EP1425277A2 (en)	2004-06-09
KR100955967B1 (ko)	2010-05-04
MY138086A (en)	2009-04-30
KR20040041610A (ko)	2004-05-17
IL160755A (en)	2009-09-01
TWI283665B (en)	2007-07-11
PT1425277E (pt)	2009-03-05
US20090163506A1 (en)	2009-06-25
KR101063679B1 (ko)	2011-09-07
AP2004002982A0 (en)	2004-03-31
CA2458632C (en)	2011-08-23
PE20030417A1 (es)	2003-08-06
MXPA04002379A (es)	2004-05-31
IL160755A0 (en)	2004-08-31
KR20100082390A (ko)	2010-07-16
WO2003022809A2 (en)	2003-03-20
PL369026A1 (en)	2005-04-18
HK1066534A1 (en)	2005-03-24
EP2298757A3 (en)	2011-12-28
KR20090026369A (ko)	2009-03-12
CN1553905A (zh)	2004-12-08
HUP0401923A2 (hu)	2005-01-28
ES2316607T3 (es)	2009-04-16
DK1425277T3 (da)	2009-03-16
CY1109449T1 (el)	2014-08-13
EP2036902A2 (en)	2009-03-18
NO20085078L (no)	2004-06-04
CA2458632A1 (en)	2003-03-20
EA200400432A1 (ru)	2004-12-30
EP2298757A2 (en)	2011-03-23

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