AU1048801A - 4-carboxyamino-2-ethyl-1,2,3,4-tetrahydroquinoline crystal as cetp inhibitor - Google Patents

4-carboxyamino-2-ethyl-1,2,3,4-tetrahydroquinoline crystal as cetp inhibitor Download PDF

Info

Publication number: AU1048801A
Authority: AU; Australia
Prior art keywords: crystal; trifluoromethyl; formula; rel; quinoline
Prior art date: 1999-11-30
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

Application number

AU10488/01A

Other languages

English (en)

Inventor

Douglas John Meldrum Allen

Troy Anthony Appleton

Lyle Robinson Brostrom

Derek Lawrence Tickner

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Pfizer Products Inc

Original Assignee

Pfizer Products 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.)

1999-11-30

Filing date

2000-11-14

Publication date

2001-06-12

2000-11-14 Application filed by Pfizer Products Inc filed Critical Pfizer Products Inc

2001-06-12 Publication of AU1048801A publication Critical patent/AU1048801A/en

Status Abandoned legal-status Critical Current

Links

239000013078 crystal Substances 0.000 title claims description 98
239000003354 cholesterol ester transfer protein inhibitor Substances 0.000 title description 3
229940125881 cholesteryl ester transfer protein inhibitor Drugs 0.000 title description 3
OXMLOGDTDJEBJR-UHFFFAOYSA-N (2-ethyl-1,2,3,4-tetrahydroquinolin-4-yl)carbamic acid Chemical compound C1=CC=C2NC(CC)CC(NC(O)=O)C2=C1 OXMLOGDTDJEBJR-UHFFFAOYSA-N 0.000 title description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 80
241000124008 Mammalia Species 0.000 claims description 70
238000000034 method Methods 0.000 claims description 47
150000001875 compounds Chemical class 0.000 claims description 40
239000008194 pharmaceutical composition Substances 0.000 claims description 36
239000003085 diluting agent Substances 0.000 claims description 28
239000003937 drug carrier Substances 0.000 claims description 28
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 28
239000003981 vehicle Substances 0.000 claims description 26
201000001320 Atherosclerosis Diseases 0.000 claims description 21
HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 claims description 21
208000000563 Hyperlipoproteinemia Type II Diseases 0.000 claims description 17
201000001386 familial hypercholesterolemia Diseases 0.000 claims description 17
-1 3,5-bis-trifluoromethyl-benzyl Chemical group 0.000 claims description 13
208000032928 Dyslipidaemia Diseases 0.000 claims description 12
208000017170 Lipid metabolism disease Diseases 0.000 claims description 12
CMSGWTNRGKRWGS-NQIIRXRSSA-N torcetrapib Chemical compound COC(=O)N([C@H]1C[C@@H](CC)N(C2=CC=C(C=C21)C(F)(F)F)C(=O)OCC)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 CMSGWTNRGKRWGS-NQIIRXRSSA-N 0.000 claims description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
208000024172 Cardiovascular disease Diseases 0.000 claims description 11
208000008589 Obesity Diseases 0.000 claims description 11
235000020824 obesity Nutrition 0.000 claims description 11
208000035150 Hypercholesterolemia Diseases 0.000 claims description 10
206010002383 Angina Pectoris Diseases 0.000 claims description 9
208000037487 Endotoxemia Diseases 0.000 claims description 9
206010020772 Hypertension Diseases 0.000 claims description 9
206010021024 Hypolipidaemia Diseases 0.000 claims description 9
208000018262 Peripheral vascular disease Diseases 0.000 claims description 9
206010063837 Reperfusion injury Diseases 0.000 claims description 9
208000006011 Stroke Diseases 0.000 claims description 9
206010012601 diabetes mellitus Diseases 0.000 claims description 9
208000006575 hypertriglyceridemia Diseases 0.000 claims description 9
208000029498 hypoalphalipoproteinemia Diseases 0.000 claims description 9
238000004519 manufacturing process Methods 0.000 claims description 9
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208000010125 myocardial infarction Diseases 0.000 claims description 8
208000028867 ischemia Diseases 0.000 claims description 7
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238000000634 powder X-ray diffraction Methods 0.000 claims description 6
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238000009499 grossing Methods 0.000 claims description 4
125000006626 methoxycarbonylamino group Chemical group 0.000 claims description 3
150000003839 salts Chemical class 0.000 claims description 2
125000006493 trifluoromethyl benzyl group Chemical group 0.000 claims description 2
239000002243 precursor Substances 0.000 claims 3
KEWSCDNULKOKTG-UHFFFAOYSA-N 4-cyano-4-ethylsulfanylcarbothioylsulfanylpentanoic acid Chemical compound CCSC(=S)SC(C)(C#N)CCC(O)=O KEWSCDNULKOKTG-UHFFFAOYSA-N 0.000 claims 2
102100037637 Cholesteryl ester transfer protein Human genes 0.000 claims 2
101000880514 Homo sapiens Cholesteryl ester transfer protein Proteins 0.000 claims 2
GZVVNAWGGPWOOK-UHFFFAOYSA-N ethyl 2h-quinoline-1-carboxylate Chemical compound C1=CC=C2N(C(=O)OCC)CC=CC2=C1 GZVVNAWGGPWOOK-UHFFFAOYSA-N 0.000 claims 2
239000010685 fatty oil Substances 0.000 claims 2
230000002401 inhibitory effect Effects 0.000 claims 2
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239000000203 mixture Substances 0.000 description 29
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
239000000243 solution Substances 0.000 description 17
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 16
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
239000003112 inhibitor Substances 0.000 description 13
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
239000007787 solid Substances 0.000 description 11
238000005481 NMR spectroscopy Methods 0.000 description 10
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OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
208000029078 coronary artery disease Diseases 0.000 description 9
239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 description 9
239000000843 powder Substances 0.000 description 9
239000002002 slurry Substances 0.000 description 9
108010061846 Cholesterol Ester Transfer Proteins Proteins 0.000 description 8
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108010010234 HDL Lipoproteins Proteins 0.000 description 8
102000015779 HDL Lipoproteins Human genes 0.000 description 8
239000000463 material Substances 0.000 description 8
238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 7
102100031545 Microsomal triglyceride transfer protein large subunit Human genes 0.000 description 7
238000002072 distortionless enhancement with polarization transfer spectrum Methods 0.000 description 7
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239000003921 oil Substances 0.000 description 7
235000019198 oils Nutrition 0.000 description 7
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
239000012267 brine Substances 0.000 description 6
HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 6
239000000706 filtrate Substances 0.000 description 6
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239000012299 nitrogen atmosphere Substances 0.000 description 6
239000000047 product Substances 0.000 description 6
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HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 6
239000002904 solvent Substances 0.000 description 5
238000003756 stirring Methods 0.000 description 5
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
108010023302 HDL Cholesterol Proteins 0.000 description 4
238000008214 LDL Cholesterol Methods 0.000 description 4
108010007622 LDL Lipoproteins Proteins 0.000 description 4
102000007330 LDL Lipoproteins Human genes 0.000 description 4
PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
238000002441 X-ray diffraction Methods 0.000 description 4
239000002775 capsule Substances 0.000 description 4
229910052799 carbon Inorganic materials 0.000 description 4
239000003153 chemical reaction reagent Substances 0.000 description 4
239000002552 dosage form Substances 0.000 description 4
230000000694 effects Effects 0.000 description 4
AZFYCLSCZLWMBW-PWSUYJOCSA-N ethyl (2r,4s)-4-amino-2-ethyl-6-(trifluoromethyl)-3,4-dihydro-2h-quinoline-1-carboxylate Chemical compound FC(F)(F)C1=CC=C2N(C(=O)OCC)[C@H](CC)C[C@H](N)C2=C1 AZFYCLSCZLWMBW-PWSUYJOCSA-N 0.000 description 4
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235000001968 nicotinic acid Nutrition 0.000 description 4
239000011664 nicotinic acid Substances 0.000 description 4
KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 4
238000000524 positive electrospray ionisation mass spectrometry Methods 0.000 description 4
229920006395 saturated elastomer Polymers 0.000 description 4
239000011734 sodium Substances 0.000 description 4
239000000725 suspension Substances 0.000 description 4
ZGGHKIMDNBDHJB-NRFPMOEYSA-M (3R,5S)-fluvastatin sodium Chemical compound [Na+].C12=CC=CC=C2N(C(C)C)C(\C=C\[C@@H](O)C[C@@H](O)CC([O-])=O)=C1C1=CC=C(F)C=C1 ZGGHKIMDNBDHJB-NRFPMOEYSA-M 0.000 description 3
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 3
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 description 3
XUKUURHRXDUEBC-UHFFFAOYSA-N Atorvastatin Natural products C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CCC(O)CC(O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-UHFFFAOYSA-N 0.000 description 3
229940122502 Cholesterol absorption inhibitor Drugs 0.000 description 3
229940123239 Cholesterol synthesis inhibitor Drugs 0.000 description 3
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
241000282412 Homo Species 0.000 description 3
108010028554 LDL Cholesterol Proteins 0.000 description 3
PCZOHLXUXFIOCF-UHFFFAOYSA-N Monacolin X Natural products C12C(OC(=O)C(C)CC)CC(C)C=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 PCZOHLXUXFIOCF-UHFFFAOYSA-N 0.000 description 3
TUZYXOIXSAXUGO-UHFFFAOYSA-N Pravastatin Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CC(O)C=C21 TUZYXOIXSAXUGO-UHFFFAOYSA-N 0.000 description 3
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 description 3
239000003963 antioxidant agent Substances 0.000 description 3
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229960005370 atorvastatin Drugs 0.000 description 3
229920000080 bile acid sequestrant Polymers 0.000 description 3
GPUADMRJQVPIAS-QCVDVZFFSA-M cerivastatin sodium Chemical compound [Na+].COCC1=C(C(C)C)N=C(C(C)C)C(\C=C\[C@@H](O)C[C@@H](O)CC([O-])=O)=C1C1=CC=C(F)C=C1 GPUADMRJQVPIAS-QCVDVZFFSA-M 0.000 description 3
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XRHSGPZKFZCFQU-ZFNKBKEPSA-N ethyl (2r,4s)-4-[[3,5-bis(trifluoromethyl)phenyl]methylamino]-2-ethyl-6-(trifluoromethyl)-3,4-dihydro-2h-quinoline-1-carboxylate;4-methylbenzenesulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1.N([C@H]1C[C@@H](CC)N(C2=CC=C(C=C21)C(F)(F)F)C(=O)OCC)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 XRHSGPZKFZCFQU-ZFNKBKEPSA-N 0.000 description 3
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SNRWAFMDCUAKHP-UHFFFAOYSA-N ethyl 2-ethyl-2-(phenylmethoxycarbonylamino)-6-(trifluoromethyl)-3,4-dihydroquinoline-1-carboxylate Chemical compound C(C)OC(=O)N1C(CCC2=CC(=CC=C12)C(F)(F)F)(CC)NC(=O)OCC1=CC=CC=C1 SNRWAFMDCUAKHP-UHFFFAOYSA-N 0.000 description 3
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Classifications

- 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
- 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
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
- 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
- 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
- A61P9/10—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
- C07D215/12—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 substituted hydrocarbon radicals attached to ring carbon atoms

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (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)
Bioinformatics & Cheminformatics (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Engineering & Computer Science (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Diabetes (AREA)
Heart & Thoracic Surgery (AREA)
Obesity (AREA)
Hematology (AREA)
Cardiology (AREA)
Communicable Diseases (AREA)
Vascular Medicine (AREA)
Emergency Medicine (AREA)
Endocrinology (AREA)
Urology & Nephrology (AREA)
Oncology (AREA)
Child & Adolescent Psychology (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Cephalosporin Compounds (AREA)
Quinoline Compounds (AREA)

AU10488/01A 1999-11-30 2000-11-14 4-carboxyamino-2-ethyl-1,2,3,4-tetrahydroquinoline crystal as cetp inhibitor Abandoned AU1048801A (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US16805199P	1999-11-30	1999-11-30
US60168051		1999-11-30
PCT/IB2000/001650 WO2001040190A1 (en)	1999-11-30	2000-11-14	4-carboxyamino-2-ethyl-1,2,3,4-tetrahydroquinoline crystal as cetp inhibitor

Publications (1)

Publication Number	Publication Date
AU1048801A true AU1048801A (en)	2001-06-12

Family

ID=22609901

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
AU10488/01A Abandoned AU1048801A (en)	1999-11-30	2000-11-14	4-carboxyamino-2-ethyl-1,2,3,4-tetrahydroquinoline crystal as cetp inhibitor

Country Status (28)

Country	Link
EP (1)	EP1246804A1 (et)
JP (1)	JP2003515592A (et)
KR (1)	KR20020058057A (et)
CN (1)	CN1402711A (et)
AP (1)	AP2002002531A0 (et)
AU (1)	AU1048801A (et)
BG (1)	BG106854A (et)
BR (1)	BR0015836A (et)
CA (1)	CA2392979A1 (et)
CO (1)	CO5271716A1 (et)
EA (1)	EA200200510A1 (et)
EC (1)	ECSP003792A (et)
EE (1)	EE200200277A (et)
GT (1)	GT200000199A (et)
HU (1)	HUP0203521A2 (et)
IL (1)	IL149097A0 (et)
IS (1)	IS6338A (et)
MA (1)	MA26845A1 (et)
MX (1)	MXPA02005354A (et)
NO (1)	NO20022558D0 (et)
OA (1)	OA12099A (et)
PA (1)	PA8506301A1 (et)
PE (1)	PE20010904A1 (et)
PL (1)	PL355892A1 (et)
TN (1)	TNSN00231A1 (et)
TR (1)	TR200201446T2 (et)
UY (1)	UY26454A1 (et)
WO (1)	WO2001040190A1 (et)

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GT200200170A (es) *	2001-09-28	2003-05-23		Preparacion de inhibidor de cetp anhidro
WO2003063822A2 (en) *	2002-02-01	2003-08-07	Pfizer Products Inc.	Method for making homogeneous spray-dried solid amorphous drug dispersions utilizing modified spray-drying apparatus
ATE395044T1 (de)	2002-02-01	2008-05-15	Pfizer Prod Inc	Pharmazeutische zusammensetzungen amorpher dispersionen von wirkstoffen und lipophiler mikrophasenbildender materialien
EP1920766B1 (en) *	2002-02-01	2017-08-23	Bend Research, Inc	Pharmaceutical compositions of amorphous dispersions of drugs and lipophilic microphase-forming materials
RU2293078C2 (ru)	2002-08-30	2007-02-10	Джапан Тобакко Инк.	Соединения дибензиламина, фармацевтическая композиция и терапевтический или профилактический агент на их основе, способ лечения или профилактики гиперлипидемии или артериосклероза
CA2500582A1 (en)	2002-10-04	2004-04-22	Millennium Pharmaceuticals, Inc.	Pgd2 receptor antagonists for the treatment of inflammatory diseases
US7504508B2 (en)	2002-10-04	2009-03-17	Millennium Pharmaceuticals, Inc.	PGD2 receptor antagonists for the treatment of inflammatory diseases
ATE461700T1 (de)	2002-12-20	2010-04-15	Pfizer Prod Inc	Dosierungsform enthaltend einen cetp-hemmer und einen hmg-coa reduktase hemmer
US20040132771A1 (en) *	2002-12-20	2004-07-08	Pfizer Inc	Compositions of choleseteryl ester transfer protein inhibitors and HMG-CoA reductase inhibitors
AU2004222436A1 (en)	2003-03-17	2004-09-30	Japan Tobacco Inc.	Method for increasing the oral bioavailability of S-(2-(((1- (2-ethylbutyl) cyclohexyl)carbonyl) amino) phenyl)-2-methylpropanethioate
EP1622872A1 (en) *	2003-03-28	2006-02-08	Pfizer Products Inc.	1,2,4-substituerte 1,2,3,4-tetrahydro-and 1,2 dihydro-quinoline and 1,2,3,4-tetrahydro-quinoxaline derivatives as cetp inhibitors for the treatment of atherosclerosis and obesity
ATE540671T1 (de)	2003-08-04	2012-01-15	Bend Res Inc	Pharmazeutische zusammensetzungen von adsorbaten von amorphen arzneimitteln und lipophilen mikrophasen-bildenden materialien
HRP20090581T1 (hr)	2003-10-08	2009-12-31	Eli Lilly And Company	Spojevi i postupci za liječenje dislipidemije
CN1942428A (zh) *	2004-04-13	2007-04-04	默克公司	Cetp抑制剂
MXPA06014716A (es) *	2004-06-24	2007-03-12	Lilly Co Eli	Compuestos y metodos para el tratamiento de dislipidemia.
WO2006033001A1 (en) *	2004-09-23	2006-03-30	Pfizer Products Inc.	Quinoline compounds
WO2006033004A1 (en) *	2004-09-23	2006-03-30	Pfizer Products Inc.	Quinoline compounds as cetp inhibitors
WO2006091674A1 (en)	2005-02-24	2006-08-31	Millennium Pharmaceuticals, Inc.	Pgd2 receptor antagonists for the treatment of inflammatory diseases
WO2006098394A1 (ja) *	2005-03-14	2006-09-21	Japan Tobacco Inc.	脂質吸収抑制方法および脂質吸収抑制剤
US7737155B2 (en)	2005-05-17	2010-06-15	Schering Corporation	Nitrogen-containing heterocyclic compounds and methods of use thereof
EP2134169A2 (en)	2007-03-09	2009-12-23	Indigene Pharmaceuticals Inc.	Combination of metformin r-(+) lipoate and antihyperlipidemic agents for the treatment of diabetic hyperglycemia and diabetic complications
US20110243940A1 (en)	2008-12-16	2011-10-06	Schering Corporation	Bicyclic pyranone derivatives and methods of use thereof
EP2379547A1 (en)	2008-12-16	2011-10-26	Schering Corporation	Pyridopyrimidine derivatives and methods of use thereof
AR077208A1 (es)	2009-06-30	2011-08-10	Lilly Co Eli	Derivados del acido trans-4-[[(5s)-5-[[[3,5-bis(trifluorometil) fenil] metil] (2-metil-2h-tetrazol-5-il) amino) -2,3,4,5-tetrahidro-7,9-dimetil-1h-1-benzazepin-1-il) metil)-ciclohexancarboxilico y sus formas cristalinas, composiciones farmaceuticas que los comprenden, su uso para preparar un medicam
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US5231102A (en) *	1989-03-08	1993-07-27	Merck Sharp & Dohme, Ltd.	Tetrahydroquinoline derivatives useful for neurodegenerative disorders
WO1998033775A1 (en) *	1997-02-03	1998-08-06	American Home Products Corporation	2-substituted-1-acyl-1,2-dihydroquinoline derivatives to increase hdl-cholesterol level
US6197786B1 (en) *	1998-09-17	2001-03-06	Pfizer Inc	4-Carboxyamino-2-substituted-1,2,3,4-tetrahydroquinolines

2000
- 2000-11-09 CO CO00085285A patent/CO5271716A1/es unknown
- 2000-11-13 PA PA20008506301A patent/PA8506301A1/es unknown
- 2000-11-14 TR TR2002/01446T patent/TR200201446T2/xx unknown
- 2000-11-14 EP EP00971662A patent/EP1246804A1/en not_active Withdrawn
- 2000-11-14 BR BR0015836-4A patent/BR0015836A/pt not_active IP Right Cessation
- 2000-11-14 AP APAP/P/2002/002531A patent/AP2002002531A0/en unknown
- 2000-11-14 EA EA200200510A patent/EA200200510A1/ru unknown
- 2000-11-14 WO PCT/IB2000/001650 patent/WO2001040190A1/en not_active Ceased
- 2000-11-14 CN CN00816463A patent/CN1402711A/zh active Pending
- 2000-11-14 EE EEP200200277A patent/EE200200277A/et unknown
- 2000-11-14 AU AU10488/01A patent/AU1048801A/en not_active Abandoned
- 2000-11-14 HU HU0203521A patent/HUP0203521A2/hu unknown
- 2000-11-14 PL PL00355892A patent/PL355892A1/xx not_active Application Discontinuation
- 2000-11-14 IL IL14909700A patent/IL149097A0/xx unknown
- 2000-11-14 CA CA002392979A patent/CA2392979A1/en not_active Abandoned
- 2000-11-14 MX MXPA02005354A patent/MXPA02005354A/es unknown
- 2000-11-14 JP JP2001541875A patent/JP2003515592A/ja active Pending
- 2000-11-14 KR KR1020027006914A patent/KR20020058057A/ko not_active Ceased
- 2000-11-14 OA OA1200200158A patent/OA12099A/en unknown
- 2000-11-28 UY UY26454A patent/UY26454A1/es not_active Application Discontinuation
- 2000-11-28 PE PE2000001267A patent/PE20010904A1/es not_active Application Discontinuation
- 2000-11-29 TN TNTNSN00231A patent/TNSN00231A1/fr unknown
- 2000-11-29 EC EC2000003792A patent/ECSP003792A/es unknown
- 2000-11-29 GT GT200000199A patent/GT200000199A/es unknown
2002
- 2002-04-12 IS IS6338A patent/IS6338A/is unknown
- 2002-05-27 MA MA26653A patent/MA26845A1/fr unknown
- 2002-05-29 NO NO20022558A patent/NO20022558D0/no not_active Application Discontinuation
- 2002-06-20 BG BG106854A patent/BG106854A/bg unknown

Also Published As

Publication number	Publication date
IL149097A0 (en)	2002-11-10
BR0015836A (pt)	2002-08-06
HUP0203521A2 (hu)	2003-02-28
PE20010904A1 (es)	2001-09-10
JP2003515592A (ja)	2003-05-07
CA2392979A1 (en)	2001-06-07
PA8506301A1 (es)	2002-08-26
BG106854A (bg)	2002-12-29
ECSP003792A (es)	2002-04-23
WO2001040190A1 (en)	2001-06-07
KR20020058057A (ko)	2002-07-12
CN1402711A (zh)	2003-03-12
EP1246804A1 (en)	2002-10-09
UY26454A1 (es)	2001-07-31
MA26845A1 (fr)	2004-12-20
EE200200277A (et)	2003-10-15
MXPA02005354A (es)	2002-12-11
OA12099A (en)	2006-05-04
GT200000199A (es)	2002-05-23
NO20022558L (no)	2002-05-29
PL355892A1 (en)	2004-05-31
TR200201446T2 (tr)	2002-11-21
IS6338A (is)	2002-04-12
EA200200510A1 (ru)	2002-10-31
TNSN00231A1 (fr)	2002-05-30
AP2002002531A0 (en)	2002-06-30
CO5271716A1 (es)	2003-04-30
NO20022558D0 (no)	2002-05-29

Publication	Publication Date	Title
AU1048801A (en)	2001-06-12	4-carboxyamino-2-ethyl-1,2,3,4-tetrahydroquinoline crystal as cetp inhibitor
CA2327029C (en)	2005-08-09	Method for making 4-carboxyamino-2-substituted-1,2,3,4-tetrahydroquinoline
DE69926582T2 (de)	2006-03-30	Anellierte 4-Carboxyamino-2-Methyl-1,2,3,4-Tetrahydrochinoline als CETP-Hemmer
DE69925845T2 (de)	2006-05-18	4-carboxamino-2-subsitutierte-1,2,3,4-tetrahydrochinoline als cetp inhibitoren
US6147090A (en)	2000-11-14	4-carboxyamino-2-methyl-1,2,3,4,-tetrahydroquinolines
CA2344248C (en)	2007-01-09	4-amino substituted-2-substituted-1,2,3,4-tetrahydroquinolines as cetp inhibitors
JP4108129B2 (ja)	2008-06-25	Ｅａａアンタゴニストとしてのテトラヒドロキノリン誘導体
DE102004044680B3 (de)	2006-06-08	Alkyliden-Tetrahydronaphthalinderivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Entzündungshemmer sowie diese enthaltende pharmazeutische Präparate
MXPA00011855A (en)	2002-06-05	Method for making (-)-(2r,4s)-4- [(3,5-bis- trifluoromethyl-benzyl)- methoxycarbonylamino]- 2-ethyl-6- trifluoromethyl-3,4-dihydro- 2h-quinoline- 1-carboxylic acid ethyl ester
HK1038007B (en)	2005-04-08	Method for making 4-carboxyamino-2-substituted-1,2,3,4-tetrahydroquinoline

Legal Events

Date	Code	Title	Description
2003-08-14	MK1	Application lapsed section 142(2)(a) - no request for examination in relevant period