HRP20000804A2 - Method for making 4-carboxyamino-2-substituted-1,2,3,4-tetrahydroquinoline - Google Patents

Method for making 4-carboxyamino-2-substituted-1,2,3,4-tetrahydroquinoline Download PDF

Info

Publication number: HRP20000804A2
Authority: HR; Croatia
Prior art keywords: ethyl; trifluoromethyl; quinoline; dihydro; carboxylic acid
Prior art date: 1999-11-30

Application number

HR20000804A

Other languages

English (en)

Croatian (hr)

Inventor

David Burns Damon

Robert Wayne Dugger

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.)

1999-11-30

Filing date

2000-11-22

Publication date

2001-06-30

2000-11-22 Application filed by Pfizer Prod Inc filed Critical Pfizer Prod Inc

2001-06-30 Publication of HRP20000804A2 publication Critical patent/HRP20000804A2/hr

Links

-1 4-carboxyamino-2-substituted-1,2,3,4-tetrahydroquinoline Chemical class 0.000 title claims description 32
238000000034 method Methods 0.000 title claims description 29
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 35
150000001875 compounds Chemical class 0.000 claims description 34
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 33
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 30
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 27
150000003839 salts Chemical class 0.000 claims description 21
KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 claims description 14
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 13
YONLFQNRGZXBBF-ZIAGYGMSSA-N (2r,3r)-2,3-dibenzoyloxybutanedioic acid Chemical compound O([C@@H](C(=O)O)[C@@H](OC(=O)C=1C=CC=CC=1)C(O)=O)C(=O)C1=CC=CC=C1 YONLFQNRGZXBBF-ZIAGYGMSSA-N 0.000 claims description 12
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 12
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 12
KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 9
KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 claims description 9
JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 claims description 9
CMIBUZBMZCBCAT-HZPDHXFCSA-N (2r,3r)-2,3-bis[(4-methylbenzoyl)oxy]butanedioic acid Chemical group C1=CC(C)=CC=C1C(=O)O[C@@H](C(O)=O)[C@H](C(O)=O)OC(=O)C1=CC=C(C)C=C1 CMIBUZBMZCBCAT-HZPDHXFCSA-N 0.000 claims description 8
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 8
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 claims description 8
238000010438 heat treatment Methods 0.000 claims description 7
HVOAACKKZXUIKP-UHFFFAOYSA-N n-[1-(benzotriazol-1-yl)propyl]-4-(trifluoromethyl)aniline Chemical compound N1=NC2=CC=CC=C2N1C(CC)NC1=CC=C(C(F)(F)F)C=C1 HVOAACKKZXUIKP-UHFFFAOYSA-N 0.000 claims description 7
LDWLIXZSDPXYDR-UHFFFAOYSA-N 3,5-bis(trifluoromethyl)benzaldehyde Chemical compound FC(F)(F)C1=CC(C=O)=CC(C(F)(F)F)=C1 LDWLIXZSDPXYDR-UHFFFAOYSA-N 0.000 claims description 6
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 6
VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 claims description 6
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 claims description 6
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 6
229910000029 sodium carbonate Inorganic materials 0.000 claims description 6
239000012321 sodium triacetoxyborohydride Substances 0.000 claims description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 5
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 5
239000002002 slurry Substances 0.000 claims description 4
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
AZFYCLSCZLWMBW-UHFFFAOYSA-N ethyl 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(CC)CC(N)C2=C1 AZFYCLSCZLWMBW-UHFFFAOYSA-N 0.000 claims description 2
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HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
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VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
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NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 4
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ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
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150000001412 amines Chemical class 0.000 description 3
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ODGIMMLDVSWADK-UHFFFAOYSA-N 4-trifluoromethylaniline Chemical compound NC1=CC=C(C(F)(F)F)C=C1 ODGIMMLDVSWADK-UHFFFAOYSA-N 0.000 description 2
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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 2
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QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 2
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NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
229940038472 dicalcium phosphate Drugs 0.000 description 1
229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
235000005911 diet Nutrition 0.000 description 1
230000037213 diet Effects 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
239000007884 disintegrant Substances 0.000 description 1
239000003814 drug Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000013583 drug formulation Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000002526 effect on cardiovascular system Effects 0.000 description 1
XEMVTTZLLAAZLR-SMDDNHRTSA-N ethyl (2R,4S)-4-amino-2-ethyl-6-(trifluoromethyl)-3,4-dihydro-1H-quinoline-2-carboxylate Chemical compound C(C)OC(=O)[C@@]1(NC2=CC=C(C=C2[C@H](C1)N)C(F)(F)F)CC XEMVTTZLLAAZLR-SMDDNHRTSA-N 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000000284 extract Substances 0.000 description 1
201000001386 familial hypercholesterolemia Diseases 0.000 description 1
238000011049 filling Methods 0.000 description 1
239000012467 final product Substances 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
239000012530 fluid Substances 0.000 description 1
235000013355 food flavoring agent Nutrition 0.000 description 1
238000009472 formulation Methods 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
208000006575 hypertriglyceridemia Diseases 0.000 description 1
208000029498 hypoalphalipoproteinemia Diseases 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
230000001678 irradiating effect Effects 0.000 description 1
208000028867 ischemia Diseases 0.000 description 1
239000008101 lactose Substances 0.000 description 1
XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 1
244000144972 livestock Species 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
239000012528 membrane Substances 0.000 description 1
125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 1
235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
244000005700 microbiome Species 0.000 description 1
208000031225 myocardial ischemia Diseases 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
238000010899 nucleation Methods 0.000 description 1
239000004006 olive oil Substances 0.000 description 1
235000008390 olive oil Nutrition 0.000 description 1
239000006186 oral dosage form Substances 0.000 description 1
239000007968 orange flavor Substances 0.000 description 1
239000010502 orange oil Substances 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
210000005259 peripheral blood Anatomy 0.000 description 1
239000011886 peripheral blood Substances 0.000 description 1
230000037081 physical activity Effects 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
239000006187 pill Substances 0.000 description 1
229940096701 plain lipid modifying drug hmg coa reductase inhibitors Drugs 0.000 description 1
229920001592 potato starch Polymers 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
230000000207 pro-atherogenic effect Effects 0.000 description 1
235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
238000000746 purification Methods 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
238000011160 research Methods 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
208000037803 restenosis Diseases 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
229940081974 saccharin Drugs 0.000 description 1
235000019204 saccharin Nutrition 0.000 description 1
239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
230000028327 secretion Effects 0.000 description 1
ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
239000004208 shellac Substances 0.000 description 1
229940113147 shellac Drugs 0.000 description 1
235000013874 shellac Nutrition 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
230000000391 smoking effect Effects 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000003206 sterilizing agent Substances 0.000 description 1
238000003860 storage Methods 0.000 description 1
239000006190 sub-lingual tablet Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
230000002792 vascular Effects 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1

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
- 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
- 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

Landscapes

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

HR20000804A 1999-11-30 2000-11-22 Method for making 4-carboxyamino-2-substituted-1,2,3,4-tetrahydroquinoline HRP20000804A2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US16796799P	1999-11-30	1999-11-30

Publications (1)

Publication Number	Publication Date
HRP20000804A2 true HRP20000804A2 (en)	2001-06-30

Family

ID=22609556

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
HR20000804A HRP20000804A2 (en)	1999-11-30	2000-11-22	Method for making 4-carboxyamino-2-substituted-1,2,3,4-tetrahydroquinoline

Country Status (45)

Country	Link
US (1)	US6313142B1 (de)
EP (1)	EP1125929B1 (de)
JP (1)	JP3579345B2 (de)
KR (1)	KR100408177B1 (de)
CN (1)	CN1173953C (de)
AP (1)	AP2000002011A0 (de)
AR (1)	AR029775A1 (de)
AT (1)	ATE315028T1 (de)
AU (1)	AU784694B2 (de)
BG (1)	BG105009A (de)
BR (1)	BR0005636A (de)
CA (1)	CA2327029C (de)
CO (1)	CO5261552A1 (de)
CY (1)	CY1104989T1 (de)
CZ (1)	CZ20004407A3 (de)
DE (1)	DE60025317T2 (de)
DK (1)	DK1125929T3 (de)
DZ (1)	DZ3079A1 (de)
EA (1)	EA003668B1 (de)
EE (1)	EE200000659A (de)
ES (1)	ES2254109T3 (de)
GE (1)	GEP20022798B (de)
GT (1)	GT200000190A (de)
HK (1)	HK1038007A1 (de)
HN (1)	HN2000000203A (de)
HR (1)	HRP20000804A2 (de)
HU (1)	HUP0004747A3 (de)
ID (1)	ID28489A (de)
IL (1)	IL139849A (de)
IS (1)	IS5715A (de)
MA (1)	MA25223A1 (de)
NO (1)	NO20006039L (de)
NZ (1)	NZ508509A (de)
OA (1)	OA11494A (de)
PA (1)	PA8503801A1 (de)
PE (1)	PE20010913A1 (de)
PL (1)	PL344208A1 (de)
SG (1)	SG102603A1 (de)
SK (1)	SK17792000A3 (de)
TN (1)	TNSN00230A1 (de)
TW (1)	TW591016B (de)
UA (1)	UA65615C2 (de)
UY (1)	UY26451A1 (de)
YU (1)	YU71500A (de)
ZA (1)	ZA200006947B (de)

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BR0215240A (pt) *	2001-12-19	2004-10-26	Atherogenics Inc	Derivados de calcona e seu uso no tratamento de doenças
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US7223870B2 (en) *	2002-11-01	2007-05-29	Pfizer Inc.	Methods for preparing N-arylated oxazolidinones via a copper catalyzed cross coupling reaction
WO2004056727A2 (en) *	2002-12-19	2004-07-08	Atherogenics, Inc.	Process of making chalcone derivatives
US20040132771A1 (en) *	2002-12-20	2004-07-08	Pfizer Inc	Compositions of choleseteryl ester transfer protein inhibitors and HMG-CoA reductase inhibitors
WO2004056358A1 (en)	2002-12-20	2004-07-08	Pfizer Products Inc.	Dosage forms comprising a cetp inhibitor and an hmg-coa reductase inhibitor
WO2004078730A2 (en) *	2003-03-04	2004-09-16	Takasago International Corporation	Method for producing optically active amines
KR100857759B1 (ko) *	2003-03-17	2008-09-09	니뽄 다바코 산교 가부시키가이샤	Ｃｅｔｐ 억제제의 약제학적 조성물
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TWI393560B (zh) *	2003-05-02	2013-04-21	Japan Tobacco Inc	包含ｓ-〔２（〔〔１-（２-乙基丁基）環己基〕羰基〕胺基）苯基〕２-甲基丙烷硫酯及ｈｍｇ輔酶ａ還原酶抑制劑之組合
ATE442358T1 (de) *	2003-10-08	2009-09-15	Lilly Co Eli	Verbindungen und verfahren zur behandlung von dyslipidemie
UA90269C2 (ru) *	2004-04-02	2010-04-26	Мицубиси Танабе Фарма Корпорейшн	Тетрагидрохинолиновые производные и способ их получения
JP2008504266A (ja) *	2004-06-24	2008-02-14	イーライリリーアンドカンパニー	異脂肪血症を治療するための化合物及び方法
DOP2005000123A (es)	2004-07-02	2011-07-15	Merck Sharp & Dohme	Inhibidores de cetp
WO2006033001A1 (en) *	2004-09-23	2006-03-30	Pfizer Products Inc.	Quinoline compounds
WO2006069162A1 (en) *	2004-12-20	2006-06-29	Reddy Us Therapeutics, Inc.	Novel heterocyclic compounds and their pharmaceutical compositions
BRPI0608553A2 (pt) *	2005-02-24	2010-01-12	Millennium Pharm Inc	antagonistas de receptor de pgd2 para o tratamento de doenças inflamatórias
TW200808731A (en)	2006-03-30	2008-02-16	Tanabe Seiyaku Co	A process for preparing tetrahydroquinoline derivatives
AR065670A1 (es)	2007-03-09	2009-06-24	Indigene Pharmaceuticals Inc	Combinacion de metformina r-(+) lipoato y agentes antihiperlipidemicos para el tratamiento de hiperglucemia diabetica y complicaciones diabeticas
CN101429160B (zh) *	2007-11-06	2011-10-19	上海药明康德新药开发有限公司	一种1-r-4-氨基-1,2,3,4-四氢喹啉的合成方法
TWI450896B (zh)	2009-06-30	2014-09-01	Lilly Co Eli	反式－４－〔〔（５ｓ）－５－〔〔〔３，５－雙（三氟甲基）苯基〕甲基〕（２－甲基－２ｈ－四唑－５－基）胺基〕－２，３，４，５－四氫－７，９－二甲基－１ｈ－１－苯并氮呯－１－基〕甲基〕－環己基羧酸

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2000
- 2000-09-14 HN HN2000000203A patent/HN2000000203A/es unknown
- 2000-09-27 PA PA20008503801A patent/PA8503801A1/es unknown
- 2000-09-29 OA OA1200000268A patent/OA11494A/en unknown
- 2000-10-10 US US09/684,830 patent/US6313142B1/en not_active Expired - Fee Related
- 2000-11-03 GT GT200000190A patent/GT200000190A/es unknown
- 2000-11-09 CO CO00085289A patent/CO5261552A1/es not_active Application Discontinuation
- 2000-11-13 DE DE60025317T patent/DE60025317T2/de not_active Expired - Fee Related
- 2000-11-13 AT AT00310064T patent/ATE315028T1/de not_active IP Right Cessation
- 2000-11-13 DK DK00310064T patent/DK1125929T3/da active
- 2000-11-13 EP EP00310064A patent/EP1125929B1/de not_active Expired - Lifetime
- 2000-11-13 ES ES00310064T patent/ES2254109T3/es not_active Expired - Lifetime
- 2000-11-16 YU YU71500A patent/YU71500A/sh unknown
- 2000-11-17 IS IS5715A patent/IS5715A/is unknown
- 2000-11-22 HR HR20000804A patent/HRP20000804A2/hr not_active Application Discontinuation
- 2000-11-23 AU AU71789/00A patent/AU784694B2/en not_active Ceased
- 2000-11-23 IL IL139849A patent/IL139849A/en not_active IP Right Cessation
- 2000-11-24 TW TW089125066A patent/TW591016B/zh not_active IP Right Cessation
- 2000-11-24 SK SK1779-2000A patent/SK17792000A3/sk unknown
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- 2000-11-27 UY UY26451A patent/UY26451A1/es not_active Application Discontinuation
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- 2000-11-29 KR KR10-2000-0071527A patent/KR100408177B1/ko not_active IP Right Cessation
- 2000-11-29 NO NO20006039A patent/NO20006039L/no not_active Application Discontinuation
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- 2000-11-29 HU HU0004747A patent/HUP0004747A3/hu unknown
- 2000-11-29 TN TNTNSN00230A patent/TNSN00230A1/fr unknown
- 2000-11-29 AR ARP000106287A patent/AR029775A1/es unknown
- 2000-11-29 EA EA200001129A patent/EA003668B1/ru not_active IP Right Cessation
- 2000-11-30 BG BG105009A patent/BG105009A/xx unknown
- 2000-11-30 BR BR0005636-7A patent/BR0005636A/pt not_active Application Discontinuation
- 2000-11-30 GE GEAP20005651A patent/GEP20022798B/en unknown
- 2000-11-30 EE EEP200000659A patent/EE200000659A/xx unknown
- 2000-11-30 PL PL00344208A patent/PL344208A1/xx not_active Application Discontinuation
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2001
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2006
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Also Published As

Publication number	Publication date
EP1125929A1 (de)	2001-08-22
UA65615C2 (uk)	2004-04-15
CA2327029A1 (en)	2001-05-30
AP2000002011A0 (en)	2000-12-31
ZA200006947B (en)	2002-05-27
EA003668B1 (ru)	2003-08-28
IL139849A0 (en)	2002-02-10
IS5715A (is)	2001-05-31
EA200001129A2 (ru)	2001-06-25
KR20010052012A (ko)	2001-06-25
GEP20022798B (en)	2002-09-25
UY26451A1 (es)	2001-06-29
DE60025317D1 (de)	2006-03-30
CZ20004407A3 (cs)	2002-06-12
HU0004747D0 (de)	2001-02-28
NZ508509A (en)	2001-06-29
PE20010913A1 (es)	2001-09-10
CO5261552A1 (es)	2003-03-31
ATE315028T1 (de)	2006-02-15
NO20006039D0 (no)	2000-11-29
GT200000190A (es)	2002-04-27
JP2001163859A (ja)	2001-06-19
TW591016B (en)	2004-06-11
EE200000659A (et)	2001-08-15
HUP0004747A2 (hu)	2001-10-28
IL139849A (en)	2006-10-31
HN2000000203A (es)	2001-06-13
CY1104989T1 (el)	2010-03-03
DE60025317T2 (de)	2006-08-03
DK1125929T3 (da)	2006-04-03
YU71500A (sh)	2003-02-28
KR100408177B1 (ko)	2003-12-01
CN1302800A (zh)	2001-07-11
HUP0004747A3 (en)	2002-12-28
PA8503801A1 (es)	2002-07-30
TNSN00230A1 (fr)	2005-11-10
CA2327029C (en)	2005-08-09
OA11494A (en)	2004-05-07
AU7178900A (en)	2001-05-31
EA200001129A3 (ru)	2001-10-22
ES2254109T3 (es)	2006-06-16
ID28489A (id)	2001-05-31
SG102603A1 (en)	2004-03-26
AU784694B2 (en)	2006-06-01
HK1038007A1 (en)	2002-03-01
AR029775A1 (es)	2003-07-16
DZ3079A1 (fr)	2004-10-24
BR0005636A (pt)	2001-07-17
EP1125929B1 (de)	2006-01-04
BG105009A (en)	2001-11-30
CN1173953C (zh)	2004-11-03
JP3579345B2 (ja)	2004-10-20
PL344208A1 (en)	2001-06-04
MA25223A1 (fr)	2001-07-02
SK17792000A3 (sk)	2002-10-08
NO20006039L (no)	2001-05-31
US6313142B1 (en)	2001-11-06

Legal Events

Date	Code	Title
2001-06-30	A1OB	Publication of a patent application
2001-11-20	AIPI	Request for the grant of a patent on the basis of a substantive examination of a patent application
2007-09-24	ODBC	Application rejected

Publication	Publication Date	Title
HRP20000804A2 (en)	2001-06-30	Method for making 4-carboxyamino-2-substituted-1,2,3,4-tetrahydroquinoline
DE69917400T2 (de)	2005-05-19	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
DE69917790T2 (de)	2005-06-09	4-amino substituierte -2-subsituierte-1,2,3,4-tetrahydrochinoline als cetp inhibitoren
DE69920727T2 (de)	2006-03-09	4-carboxamino-2-methyl-1,2,3,4-tetrahydrochinoline als cetp inhibitoren
MXPA02005354A (es)	2002-12-11	Cristal de 4-carboxamino-1,2,3,4-tetrahidroquinolina 2-sustituida.
EP0344519B1 (de)	1993-04-14	Substituierte 4-(Chinolin-2-yl-methoxy)phenyl-essigsäure-Derivate
EP0346208B1 (de)	1994-04-13	4-Amino-chinoline und Naphthyridine, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel
CN113195084B (zh)	2024-04-09	可用作分子伴侣介导的自噬调节剂的苯并噁唑及相关化合物
DE3617183A1 (de)	1987-05-27	Substituierte benzylether
CA1263957A (fr)	1989-12-19	Derives quinolylglycinamides, leur procede de preparation et leur application therapeutique en tant que psychotropes
US20100152447A1 (en)	2010-06-17	Novel Method for Producing 4,4-(1-Methyl-1,2-Ethanediyl)-BIS-(2,6-Piperazinedione)
US11834424B2 (en)	2023-12-05	Compounds useful as chaperone-mediated autophagy modulators
EP0062919B1 (de)	1986-07-30	Neue Indol-Derivate, Verfahren zu ihrer Herstellung und pharmazeutische Präparate, die diese Verbindungen enthalten
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