UA68390C2 - 4-carboxamine-2-substituted-1,2,3,4-tetrahydroquinolines as cholesteryl ester transfer protein inhibitors - Google Patents

4-carboxamine-2-substituted-1,2,3,4-tetrahydroquinolines as cholesteryl ester transfer protein inhibitors Download PDF

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Publication number: UA68390C2
Authority: UA; Ukraine
Prior art keywords: optionally; alkyl; mono; substituted; oxo
Prior art date: 1998-09-17

Application number

UA2001031790A

Other languages

English (en)

Ukrainian (uk)

Original Assignee

Pfizer Prod Inc

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.)

1998-09-17

Filing date

1999-10-09

Publication date

2004-08-16

1999-10-09 Application filed by Pfizer Prod Inc filed Critical Pfizer Prod Inc

2004-08-16 Publication of UA68390C2 publication Critical patent/UA68390C2/uk

Links

239000003354 cholesterol ester transfer protein inhibitor Substances 0.000 title abstract 2
150000001875 compounds Chemical class 0.000 claims abstract description 433
239000000651 prodrug Substances 0.000 claims abstract description 133
229940002612 prodrug Drugs 0.000 claims abstract description 133
150000003839 salts Chemical class 0.000 claims abstract description 113
241000124008 Mammalia Species 0.000 claims abstract description 82
239000003112 inhibitor Substances 0.000 claims abstract description 79
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 33
201000001320 Atherosclerosis Diseases 0.000 claims abstract description 29
208000024172 Cardiovascular disease Diseases 0.000 claims abstract description 18
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 238
229920006395 saturated elastomer Polymers 0.000 claims description 206
125000000217 alkyl group Chemical group 0.000 claims description 184
-1 4-Carboxyamino-2-substituted-1,2,3,4-tetrahydroquinolines Chemical class 0.000 claims description 157
229910052757 nitrogen Chemical group 0.000 claims description 151
125000004043 oxo group Chemical class O=* 0.000 claims description 149
229910052717 sulfur Inorganic materials 0.000 claims description 132
229910052736 halogen Inorganic materials 0.000 claims description 120
150000002367 halogens Chemical class 0.000 claims description 120
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 109
239000011593 sulfur Chemical group 0.000 claims description 109
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 108
125000005842 heteroatom Chemical group 0.000 claims description 108
229910052760 oxygen Inorganic materials 0.000 claims description 108
239000001301 oxygen Substances 0.000 claims description 108
238000000034 method Methods 0.000 claims description 106
229910052799 carbon Inorganic materials 0.000 claims description 97
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 94
125000001153 fluoro group Chemical group F* 0.000 claims description 85
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 74
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 66
125000001424 substituent group Chemical group 0.000 claims description 66
125000004093 cyano group Chemical group *C#N 0.000 claims description 62
239000000203 mixture Substances 0.000 claims description 62
125000003545 alkoxy group Chemical group 0.000 claims description 59
125000004414 alkyl thio group Chemical group 0.000 claims description 53
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 53
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230000001225 therapeutic effect Effects 0.000 claims description 28
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150000002430 hydrocarbons Chemical class 0.000 claims description 24
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208000035150 Hypercholesterolemia Diseases 0.000 claims description 22
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QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 13
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PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 8
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PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims description 8
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XUKUURHRXDUEBC-KAYWLYCHSA-N Atorvastatin Chemical compound C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-KAYWLYCHSA-N 0.000 claims description 7
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RYMZZMVNJRMUDD-UHFFFAOYSA-N SJ000286063 Natural products C12C(OC(=O)C(C)(C)CC)CC(C)C=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 RYMZZMVNJRMUDD-UHFFFAOYSA-N 0.000 claims description 7
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XBPMXUYSYAIPTR-UHFFFAOYSA-N propan-2-yl 2h-quinoline-1-carboxylate Chemical compound C1=CC=C2N(C(=O)OC(C)C)CC=CC2=C1 XBPMXUYSYAIPTR-UHFFFAOYSA-N 0.000 claims 1
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URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
239000001509 sodium citrate Substances 0.000 description 1
NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
229910052979 sodium sulfide Inorganic materials 0.000 description 1
GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000008247 solid mixture Substances 0.000 description 1
241000894007 species Species 0.000 description 1
230000002269 spontaneous effect Effects 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
239000010959 steel Substances 0.000 description 1
230000004936 stimulating effect Effects 0.000 description 1
238000003860 storage Methods 0.000 description 1
239000007929 subcutaneous injection Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
239000013589 supplement Substances 0.000 description 1
230000001629 suppression Effects 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
GVOUNNPTGXEMIM-UHFFFAOYSA-N tert-butyl 2h-quinoline-1-carboxylate Chemical compound C1=CC=C2N(C(=O)OC(C)(C)C)CC=CC2=C1 GVOUNNPTGXEMIM-UHFFFAOYSA-N 0.000 description 1
UOUFRTFWWBCVPV-UHFFFAOYSA-N tert-butyl 4-(2,4-dioxo-1H-thieno[3,2-d]pyrimidin-3-yl)piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(CC1)n1c(=O)[nH]c2ccsc2c1=O UOUFRTFWWBCVPV-UHFFFAOYSA-N 0.000 description 1
AZAKMLHUDVIDFN-UHFFFAOYSA-N tert-butyl nitrate Chemical compound CC(C)(C)O[N+]([O-])=O AZAKMLHUDVIDFN-UHFFFAOYSA-N 0.000 description 1
125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
238000012360 testing method Methods 0.000 description 1
150000003530 tetrahydroquinolines Chemical class 0.000 description 1
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
150000003573 thiols Chemical class 0.000 description 1
210000000115 thoracic cavity Anatomy 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
230000008359 toxicosis Effects 0.000 description 1
238000002627 tracheal intubation Methods 0.000 description 1
230000002103 transcriptional effect Effects 0.000 description 1
239000006211 transdermal dosage form Substances 0.000 description 1
238000000844 transformation Methods 0.000 description 1
230000009261 transgenic effect Effects 0.000 description 1
229910052723 transition metal Inorganic materials 0.000 description 1
150000003624 transition metals Chemical class 0.000 description 1
230000005945 translocation Effects 0.000 description 1
238000002054 transplantation Methods 0.000 description 1
230000032258 transport 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
NAWZSHBMUXXTGV-UHFFFAOYSA-M triethyl(hexyl)azanium;bromide Chemical compound [Br-].CCCCCC[N+](CC)(CC)CC NAWZSHBMUXXTGV-UHFFFAOYSA-M 0.000 description 1
ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
FBXGIVCVOWMMNI-UHFFFAOYSA-L trifluoromethanesulfonate;ytterbium(2+) Chemical compound [Yb+2].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F FBXGIVCVOWMMNI-UHFFFAOYSA-L 0.000 description 1
229910052722 tritium Inorganic materials 0.000 description 1
229960000281 trometamol Drugs 0.000 description 1
208000001072 type 2 diabetes mellitus Diseases 0.000 description 1
238000005199 ultracentrifugation Methods 0.000 description 1
150000003672 ureas Chemical class 0.000 description 1
238000010792 warming Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1
235000005074 zinc chloride Nutrition 0.000 description 1
150000003952 β-lactams Chemical class 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- 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
- A61P3/04—Anorexiants; Antiobesity agents
- 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
- A61P3/06—Antihyperlipidemics
- 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
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
- A61P39/02—Antidotes
- 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
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
- A—HUMAN NECESSITIES
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- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- 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
- A61P9/12—Antihypertensives
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/38—Nitrogen atoms
- C07D215/42—Nitrogen atoms attached in position 4
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/06—Ring systems of three rings
- C07D221/16—Ring systems of three rings containing carbocyclic rings other than six-membered
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Diabetes (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Hematology (AREA)
Obesity (AREA)
Epidemiology (AREA)
Emergency Medicine (AREA)
Child & Adolescent Psychology (AREA)
Toxicology (AREA)
Urology & Nephrology (AREA)
Vascular Medicine (AREA)
Endocrinology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Quinoline Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Steroid Compounds (AREA)

UA2001031790A 1998-09-17 1999-10-09 4-carboxamine-2-substituted-1,2,3,4-tetrahydroquinolines as cholesteryl ester transfer protein inhibitors UA68390C2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US10086098P	1998-09-17	1998-09-17
PCT/IB1999/001532 WO2000017164A1 (en)	1998-09-17	1999-09-10	4-carboxyamino-2-substituted-1,2,3,4-tetrahydroquinolines as cetp inhibitors

Publications (1)

Publication Number	Publication Date
UA68390C2 true UA68390C2 (en)	2004-08-16

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UA2001031790A UA68390C2 (en)	1998-09-17	1999-10-09	4-carboxamine-2-substituted-1,2,3,4-tetrahydroquinolines as cholesteryl ester transfer protein inhibitors

Country Status (47)

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US (4)	US6197786B1 (id)
EP (1)	EP1114031B1 (id)
JP (3)	JP3626685B2 (id)
KR (1)	KR100428330B1 (id)
CN (1)	CN1331858C (id)
AP (1)	AP1346A (id)
AR (1)	AR021481A1 (id)
AT (1)	ATE297898T1 (id)
AU (1)	AU752566B2 (id)
BG (1)	BG65125B1 (id)
BR (1)	BR9913810A (id)
CA (1)	CA2344350C (id)
CO (1)	CO5370678A1 (id)
CR (1)	CR6310A (id)
CU (1)	CU23082A3 (id)
CZ (1)	CZ2001955A3 (id)
DE (1)	DE69925845T2 (id)
DK (1)	DK1114031T3 (id)
DZ (1)	DZ2890A1 (id)
EA (1)	EA004674B1 (id)
EE (1)	EE200100166A (id)
ES (1)	ES2243069T3 (id)
GE (1)	GEP20033051B (id)
GT (1)	GT199900150A (id)
HK (1)	HK1040243A1 (id)
HN (1)	HN1999000154A (id)
HR (1)	HRP20010201A2 (id)
HU (1)	HUP0103506A3 (id)
ID (1)	ID28026A (id)
IL (3)	IL141505A0 (id)
IS (1)	IS5859A (id)
MA (1)	MA26688A1 (id)
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OA (1)	OA11650A (id)
PA (1)	PA8481401A1 (id)
PE (1)	PE20001069A1 (id)
PL (1)	PL347099A1 (id)
PT (1)	PT1114031E (id)
SK (1)	SK3542001A3 (id)
TN (1)	TNSN99171A1 (id)
TR (1)	TR200100768T2 (id)
TW (1)	TWI242007B (id)
UA (1)	UA68390C2 (id)
WO (1)	WO2000017164A1 (id)
YU (1)	YU16501A (id)

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NO20011350L (no)	2001-05-09
JP3626685B2 (ja)	2005-03-09
HUP0103506A2 (hu)	2002-01-28
SK3542001A3 (en)	2002-06-04
NO318830B1 (no)	2005-05-09
MA26688A1 (fr)	2004-12-20
EA004674B1 (ru)	2004-06-24
PE20001069A1 (es)	2000-10-19
BG65125B1 (bg)	2007-03-30
KR20010085813A (ko)	2001-09-07
TNSN99171A1 (fr)	2005-11-10
CN1318058A (zh)	2001-10-17
IS5859A (is)	2001-02-23
AU5440199A (en)	2000-04-10
AP1346A (en)	2004-12-15
CZ2001955A3 (cs)	2001-12-12
EP1114031B1 (en)	2005-06-15
AR021481A1 (es)	2002-07-24
EE200100166A (et)	2002-06-17
WO2000017164A1 (en)	2000-03-30
DK1114031T3 (da)	2005-09-12
DZ2890A1 (fr)	2003-12-15
OA11650A (en)	2004-12-07
JP2002526475A (ja)	2002-08-20
PL347099A1 (en)	2002-03-25
EA200100202A1 (ru)	2001-10-22
NO20011350D0 (no)	2001-03-16
BG105428A (en)	2002-01-31
YU16501A (sh)	2004-05-12
GEP20033051B (en)	2003-08-25
HRP20010201A2 (en)	2002-04-30
CU23082A3 (es)	2005-08-17
ID28026A (id)	2001-05-03
TR200100768T2 (tr)	2001-07-23
MY130670A (en)	2007-07-31
BR9913810A (pt)	2001-06-19
CO5370678A1 (es)	2004-02-27
JP2006188542A (ja)	2006-07-20
HUP0103506A3 (en)	2002-11-28
PA8481401A1 (es)	2002-02-21
ATE297898T1 (de)	2005-07-15
CA2344350C (en)	2007-01-02
IL141505A (en)	2007-02-11
EP1114031A1 (en)	2001-07-11
JP2004339239A (ja)	2004-12-02
IL141505A0 (en)	2002-03-10
AU752566B2 (en)	2002-09-19
CA2344350A1 (en)	2000-03-30
US6586448B1 (en)	2003-07-01
CR6310A (es)	2003-11-25
US20040092550A1 (en)	2004-05-13
US6906082B2 (en)	2005-06-14
PT1114031E (pt)	2005-09-30
DE69925845T2 (de)	2006-05-18
HK1040243A1 (zh)	2002-05-31
US20050245570A1 (en)	2005-11-03
GT199900150A (es)	2001-03-03
KR100428330B1 (ko)	2004-04-28
NZ509840A (en)	2002-11-26
DE69925845D1 (en)	2005-07-21
IL173393A0 (en)	2006-06-11
CN1331858C (zh)	2007-08-15
TWI242007B (en)	2005-10-21
US6197786B1 (en)	2001-03-06
AP2001002101A0 (en)	2001-03-31
ES2243069T3 (es)	2005-11-16
HN1999000154A (es)	2000-01-12

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JP3561474B2 (ja)	2004-09-02	Ｃｅｔｐ阻害剤としての４−アミノ置換−２−置換−１，２，３，４−テトラヒドロキノリン
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DE69920727T2 (de)	2006-03-09	4-carboxamino-2-methyl-1,2,3,4-tetrahydrochinoline als cetp inhibitoren
CA2282183C (en)	2006-08-08	Oxy substituted 4-carboxyamino-2-methyl-1,2,3,4-tetrahydroquinolines
JP3469829B2 (ja)	2003-11-25	環化４−カルボキシアミノ−２−メチル−１，２，３，４−テトラヒドロキノリン
MXPA99008584A (en)	2000-08-01	4-carboxyamino-2-methyl-1,2,3,4-tetrahidroquinolinas oxi-substitui
AU2772802A (en)	2002-05-16	4-carboxyamino-2-substituted-1,2,3,4-tetrahydroquinolines as CETP inhibitors
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