UA78708C2 - Substituted naphtyl indol derivatives as inhibitors of plasminogen activator inhibitor type i (pai-1) - Google Patents

Substituted naphtyl indol derivatives as inhibitors of plasminogen activator inhibitor type i (pai-1) Download PDF

Info

Publication number: UA78708C2
Authority: UA; Ukraine
Prior art keywords: carbon atoms; pentyl; naphthyl; alkyl; benzyl
Prior art date: 2001-06-20

Application number

UA2004010350A

Other languages

English (en)

Ukrainian (uk)

Inventor

Scott Christian Mayer

Eric Gould Gundersen

Hassan Mahmoud Elokdah

David Leroy Crandall

Original Assignee

Wyeth Corp

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.)

2001-06-20

Filing date

2002-06-18

Publication date

2007-04-25

2002-06-18 Application filed by Wyeth Corp filed Critical Wyeth Corp

2007-04-25 Publication of UA78708C2 publication Critical patent/UA78708C2/uk

Links

-1 naphtyl indol derivatives Chemical class 0.000 title claims description 17
239000003112 inhibitor Substances 0.000 title description 5
102000010752 Plasminogen Inactivators Human genes 0.000 title description 2
108010077971 Plasminogen Inactivators Proteins 0.000 title description 2
239000002797 plasminogen activator inhibitor Substances 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 140
125000000217 alkyl group Chemical group 0.000 claims abstract description 50
150000003839 salts Chemical class 0.000 claims abstract description 43
238000000034 method Methods 0.000 claims abstract description 42
238000011282 treatment Methods 0.000 claims abstract description 29
125000003118 aryl group Chemical group 0.000 claims abstract description 24
125000001589 carboacyl group Chemical group 0.000 claims abstract description 22
125000005010 perfluoroalkyl group Chemical group 0.000 claims abstract description 18
239000002253 acid Substances 0.000 claims abstract description 17
125000003545 alkoxy group Chemical group 0.000 claims abstract description 17
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 15
125000003435 aroyl group Chemical group 0.000 claims abstract description 11
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 11
125000003282 alkyl amino group Chemical group 0.000 claims abstract description 10
125000002877 alkyl aryl group Chemical group 0.000 claims abstract description 10
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 10
125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 9
229920001774 Perfluoroether Polymers 0.000 claims abstract description 6
125000000896 monocarboxylic acid group Chemical group 0.000 claims abstract description 6
PGRHXDWITVMQBC-UHFFFAOYSA-N dehydroacetic acid Natural products CC(=O)C1C(=O)OC(C)=CC1=O PGRHXDWITVMQBC-UHFFFAOYSA-N 0.000 claims abstract description 5
PEQJBOMPGWYIRO-UHFFFAOYSA-N n-ethyl-3,4-dimethoxyaniline Chemical compound CCNC1=CC=C(OC)C(OC)=C1 PEQJBOMPGWYIRO-UHFFFAOYSA-N 0.000 claims abstract description 5
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 100
229910052739 hydrogen Inorganic materials 0.000 claims description 33
239000001257 hydrogen Substances 0.000 claims description 33
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 26
239000000203 mixture Substances 0.000 claims description 26
150000002431 hydrogen Chemical class 0.000 claims description 22
229910052736 halogen Inorganic materials 0.000 claims description 21
150000002367 halogens Chemical class 0.000 claims description 21
150000002148 esters Chemical class 0.000 claims description 20
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
238000006243 chemical reaction Methods 0.000 claims description 10
239000003527 fibrinolytic agent Substances 0.000 claims description 10
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
241000124008 Mammalia Species 0.000 claims description 9
230000003480 fibrinolytic effect Effects 0.000 claims description 9
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
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WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
239000000654 additive Substances 0.000 claims description 4
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GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
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230000007062 hydrolysis Effects 0.000 claims description 4
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OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
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239000007788 liquid Substances 0.000 description 6
239000000126 substance Substances 0.000 description 6
FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical class C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 5
XEQHAEZWPZICKJ-UHFFFAOYSA-N 2-naphthalen-1-yl-1h-indole Chemical class C1=CC=C2C(C3=CC4=CC=CC=C4N3)=CC=CC2=C1 XEQHAEZWPZICKJ-UHFFFAOYSA-N 0.000 description 5
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208000024827 Alzheimer disease Diseases 0.000 description 4
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ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 4
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239000011780 sodium chloride Substances 0.000 description 4
125000001424 substituent group Chemical group 0.000 description 4
125000003107 substituted aryl group Chemical group 0.000 description 4
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YIQGLTKAOHRZOL-UHFFFAOYSA-N 2-methoxynaphthalene-1-carbaldehyde Chemical class C1=CC=CC2=C(C=O)C(OC)=CC=C21 YIQGLTKAOHRZOL-UHFFFAOYSA-N 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
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ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
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PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 3
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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UA2004010350A 2001-06-20 2002-06-18 Substituted naphtyl indol derivatives as inhibitors of plasminogen activator inhibitor type i (pai-1) UA78708C2 (en)

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US29965101P	2001-06-20	2001-06-20
PCT/US2002/021113 WO2003000684A1 (en)	2001-06-20	2002-06-18	Substituted naphthyl indole derivatives as inhibitors of plasminogen activator inhibitor type-1 (pai-1)

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CN (1)	CN1280288C (pt)
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AT (1)	ATE431346T1 (pt)
AU (1)	AU2002316533B2 (pt)
BR (1)	BR0210504A (pt)
CA (1)	CA2448798C (pt)
CO (1)	CO5540286A2 (pt)
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EA (1)	EA009696B1 (pt)
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ES (1)	ES2325733T3 (pt)
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NZ (1)	NZ530312A (pt)
PL (1)	PL367525A1 (pt)
TW (1)	TWI224101B (pt)
UA (1)	UA78708C2 (pt)
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ZA (1)	ZA200400380B (pt)

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- 2002-06-10 TW TW091112530A patent/TWI224101B/zh not_active IP Right Cessation
- 2002-06-13 US US10/171,041 patent/US6800654B2/en not_active Expired - Fee Related
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- 2002-06-18 KR KR10-2003-7016636A patent/KR20040007744A/ko active IP Right Grant
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- 2002-06-18 CN CNB028123913A patent/CN1280288C/zh not_active Expired - Fee Related
- 2002-06-18 PL PL02367525A patent/PL367525A1/xx not_active Application Discontinuation
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- 2003-12-19 CO CO03111217A patent/CO5540286A2/es not_active Application Discontinuation
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- 2004-07-20 US US10/894,618 patent/US6939886B2/en not_active Expired - Fee Related
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Also Published As

Publication number	Publication date
US6800654B2 (en)	2004-10-05
ZA200400380B (en)	2006-06-28
CO5540286A2 (es)	2005-07-29
WO2003000684A1 (en)	2003-01-03
US7629377B2 (en)	2009-12-08
US7351730B2 (en)	2008-04-01
US20040266733A1 (en)	2004-12-30
ATE431346T1 (de)	2009-05-15
AU2002316533B2 (en)	2007-10-18
JP4520144B2 (ja)	2010-08-04
EA009696B1 (ru)	2008-02-28
EP1397356B1 (en)	2009-05-13
US20030032626A1 (en)	2003-02-13
MXPA03011522A (es)	2004-03-19
CN1280288C (zh)	2006-10-18
PL367525A1 (en)	2005-02-21
AR036101A1 (es)	2004-08-11
EP1397356A1 (en)	2004-03-17
NZ530312A (en)	2005-05-27
TWI224101B (en)	2004-11-21
HUP0400233A3 (en)	2008-10-28
NO326316B1 (no)	2008-11-10
KR20040007744A (ko)	2004-01-24
NO20035635D0 (no)	2003-12-17
BR0210504A (pt)	2004-05-18
NO20084390L (no)	2003-12-17
CA2448798C (en)	2010-07-20
US20080182883A1 (en)	2008-07-31
ES2325733T3 (es)	2009-09-15
JP2004534825A (ja)	2004-11-18
IL159449A0 (en)	2004-06-01
US6939886B2 (en)	2005-09-06
CA2448798A1 (en)	2003-01-03
DE60232328D1 (de)	2009-06-25
CN1549814A (zh)	2004-11-24
HUP0400233A2 (hu)	2004-08-30
US20060014725A1 (en)	2006-01-19
ECSP034904A (es)	2004-01-28
EA200400054A1 (ru)	2004-04-29

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