BG107036A - Малоhаmови киселини и техни производни като лиганди на тироидния рецептор - Google Patents

Малоhаmови киселини и техни производни като лиганди на тироидния рецептор Download PDF

Info

Publication number: BG107036A
Authority: BG; Bulgaria
Prior art keywords: hydrogen; compound; phenyl; alkyl; methyl
Prior art date: 2000-03-31

Application number

BG107036A

Other languages

Bulgarian (bg)

English (en)

Inventor

Gary Aspnes

Yuan-Ching Chiang

Kimberly Estep

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.)

2000-03-31

Filing date

2002-08-26

Publication date

2003-04-30

2002-08-26 Application filed by Pfizer Products Inc. filed Critical Pfizer Products Inc.

2003-04-30 Publication of BG107036A publication Critical patent/BG107036A/bg

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CGJMROBVSBIBKP-UHFFFAOYSA-N malonamic acid Chemical class NC(=O)CC(O)=O CGJMROBVSBIBKP-UHFFFAOYSA-N 0.000 title abstract description 12
108090000721 thyroid hormone receptors Proteins 0.000 title abstract description 11
102000004217 thyroid hormone receptors Human genes 0.000 title abstract description 11
239000003446 ligand Substances 0.000 title abstract description 9
238000011282 treatment Methods 0.000 claims abstract description 48
206010012601 diabetes mellitus Diseases 0.000 claims abstract description 38
208000008589 Obesity Diseases 0.000 claims abstract description 36
235000020824 obesity Nutrition 0.000 claims abstract description 36
206010020772 Hypertension Diseases 0.000 claims abstract description 28
201000001320 Atherosclerosis Diseases 0.000 claims abstract description 26
208000031226 Hyperlipidaemia Diseases 0.000 claims abstract description 23
206010007559 Cardiac failure congestive Diseases 0.000 claims abstract description 19
208000035150 Hypercholesterolemia Diseases 0.000 claims abstract description 19
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 19
208000001132 Osteoporosis Diseases 0.000 claims abstract description 16
206010019280 Heart failures Diseases 0.000 claims abstract description 15
208000029078 coronary artery disease Diseases 0.000 claims abstract description 15
208000003532 hypothyroidism Diseases 0.000 claims abstract description 15
230000002989 hypothyroidism Effects 0.000 claims abstract description 15
208000010412 Glaucoma Diseases 0.000 claims abstract description 14
208000024799 Thyroid disease Diseases 0.000 claims abstract description 14
206010003119 arrhythmia Diseases 0.000 claims abstract description 13
206010033307 Overweight Diseases 0.000 claims abstract description 12
208000024770 Thyroid neoplasm Diseases 0.000 claims abstract description 11
208000017520 skin disease Diseases 0.000 claims abstract description 11
201000002510 thyroid cancer Diseases 0.000 claims abstract description 11
150000001875 compounds Chemical class 0.000 claims description 627
229910052739 hydrogen Inorganic materials 0.000 claims description 299
239000001257 hydrogen Substances 0.000 claims description 299
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 217
-1 (i) -CN Chemical class 0.000 claims description 187
125000001424 substituent group Chemical group 0.000 claims description 159
239000000651 prodrug Substances 0.000 claims description 132
229940002612 prodrug Drugs 0.000 claims description 132
125000003118 aryl group Chemical group 0.000 claims description 99
150000003839 salts Chemical class 0.000 claims description 96
125000001072 heteroaryl group Chemical group 0.000 claims description 87
150000002367 halogens Chemical class 0.000 claims description 85
125000000592 heterocycloalkyl group Chemical group 0.000 claims description 85
229910052736 halogen Inorganic materials 0.000 claims description 84
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 65
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 59
125000004043 oxo group Chemical group O=* 0.000 claims description 59
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 58
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 47
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 44
125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 42
125000000623 heterocyclic group Chemical group 0.000 claims description 40
238000002360 preparation method Methods 0.000 claims description 39
125000005842 heteroatom Chemical group 0.000 claims description 37
125000004432 carbon atom Chemical group C* 0.000 claims description 35
201000004384 Alopecia Diseases 0.000 claims description 32
239000003795 chemical substances by application Substances 0.000 claims description 32
125000000753 cycloalkyl group Chemical group 0.000 claims description 31
230000003676 hair loss Effects 0.000 claims description 31
208000024963 hair loss Diseases 0.000 claims description 28
125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 26
239000003814 drug Substances 0.000 claims description 26
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 26
150000004702 methyl esters Chemical class 0.000 claims description 26
229910052799 carbon Inorganic materials 0.000 claims description 24
125000002837 carbocyclic group Chemical group 0.000 claims description 22
125000001309 chloro group Chemical group Cl* 0.000 claims description 20
125000002619 bicyclic group Chemical group 0.000 claims description 19
125000004429 atom Chemical group 0.000 claims description 17
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 17
229910052757 nitrogen Inorganic materials 0.000 claims description 17
125000000217 alkyl group Chemical group 0.000 claims description 16
208000022531 anorexia Diseases 0.000 claims description 16
206010061428 decreased appetite Diseases 0.000 claims description 16
DHHVAGZRUROJKS-UHFFFAOYSA-N phentermine Chemical compound CC(C)(N)CC1=CC=CC=C1 DHHVAGZRUROJKS-UHFFFAOYSA-N 0.000 claims description 16
229910052717 sulfur Inorganic materials 0.000 claims description 15
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 14
125000002950 monocyclic group Chemical group 0.000 claims description 14
125000003545 alkoxy group Chemical group 0.000 claims description 13
125000004494 ethyl ester group Chemical group 0.000 claims description 13
241000124008 Mammalia Species 0.000 claims description 12
208000021510 thyroid gland disease Diseases 0.000 claims description 12
125000000304 alkynyl group Chemical group 0.000 claims description 11
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 11
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 10
125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 9
125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 9
125000001624 naphthyl group Chemical group 0.000 claims description 9
PVKYYDIPUNAQOX-UHFFFAOYSA-N 3-[4-[3-(cyclobutylmethylsulfonyl)-4-hydroxyphenoxy]-3,5-dimethylanilino]-3-oxopropanoic acid Chemical compound CC1=CC(NC(=O)CC(O)=O)=CC(C)=C1OC1=CC=C(O)C(S(=O)(=O)CC2CCC2)=C1 PVKYYDIPUNAQOX-UHFFFAOYSA-N 0.000 claims description 8
125000001153 fluoro group Chemical group F* 0.000 claims description 8
229960003562 phentermine Drugs 0.000 claims description 8
DBGIVFWFUFKIQN-UHFFFAOYSA-N (+-)-Fenfluramine Chemical compound CCNC(C)CC1=CC=CC(C(F)(F)F)=C1 DBGIVFWFUFKIQN-UHFFFAOYSA-N 0.000 claims description 7
ABFCGJGGMKHFBJ-UHFFFAOYSA-N 3-[3-chloro-4-[3-(4-fluorophenyl)sulfonyl-4-hydroxyphenoxy]-5-methylanilino]-3-oxopropanoic acid Chemical compound CC1=CC(NC(=O)CC(O)=O)=CC(Cl)=C1OC1=CC=C(O)C(S(=O)(=O)C=2C=CC(F)=CC=2)=C1 ABFCGJGGMKHFBJ-UHFFFAOYSA-N 0.000 claims description 7
229960001582 fenfluramine Drugs 0.000 claims description 7
DBGIVFWFUFKIQN-VIFPVBQESA-N (+)-Fenfluramine Chemical compound CCN[C@@H](C)CC1=CC=CC(C(F)(F)F)=C1 DBGIVFWFUFKIQN-VIFPVBQESA-N 0.000 claims description 6
HZJQOVSUPDKFFL-UHFFFAOYSA-N 3-[3,5-dichloro-4-[3-(4-fluorophenyl)sulfonyl-4-hydroxyphenoxy]anilino]-2-methyl-3-oxopropanoic acid Chemical compound ClC1=CC(NC(=O)C(C(O)=O)C)=CC(Cl)=C1OC1=CC=C(O)C(S(=O)(=O)C=2C=CC(F)=CC=2)=C1 HZJQOVSUPDKFFL-UHFFFAOYSA-N 0.000 claims description 6
HCQUAEYYTNDJIM-UHFFFAOYSA-N 3-[3-chloro-4-[3-(cyclobutylmethylsulfonyl)-4-hydroxyphenoxy]-5-methylanilino]-3-oxopropanoic acid Chemical compound CC1=CC(NC(=O)CC(O)=O)=CC(Cl)=C1OC1=CC=C(O)C(S(=O)(=O)CC2CCC2)=C1 HCQUAEYYTNDJIM-UHFFFAOYSA-N 0.000 claims description 6
OZVBMTJYIDMWIL-AYFBDAFISA-N bromocriptine Chemical compound C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)N[C@]2(C(=O)N3[C@H](C(N4CCC[C@H]4[C@]3(O)O2)=O)CC(C)C)C(C)C)C2)=C3C2=C(Br)NC3=C1 OZVBMTJYIDMWIL-AYFBDAFISA-N 0.000 claims description 6
229960002802 bromocriptine Drugs 0.000 claims description 6
229960004597 dexfenfluramine Drugs 0.000 claims description 6
UNAANXDKBXWMLN-UHFFFAOYSA-N sibutramine Chemical compound C=1C=C(Cl)C=CC=1C1(C(N(C)C)CC(C)C)CCC1 UNAANXDKBXWMLN-UHFFFAOYSA-N 0.000 claims description 6
229960004425 sibutramine Drugs 0.000 claims description 6
125000003342 alkenyl group Chemical group 0.000 claims description 5
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 5
NESCWINVDYPXMU-UHFFFAOYSA-N 3-[3-chloro-4-[3-(cyclopropylmethylsulfonyl)-4-hydroxyphenoxy]-5-methylanilino]-3-oxopropanoic acid Chemical compound CC1=CC(NC(=O)CC(O)=O)=CC(Cl)=C1OC1=CC=C(O)C(S(=O)(=O)CC2CC2)=C1 NESCWINVDYPXMU-UHFFFAOYSA-N 0.000 claims description 4
PEZKCCUGBLAYSQ-UHFFFAOYSA-N 3-[4-(3-cyclopentylsulfonyl-4-hydroxyphenoxy)-3,5-dimethylanilino]-3-oxopropanoic acid Chemical compound CC1=CC(NC(=O)CC(O)=O)=CC(C)=C1OC1=CC=C(O)C(S(=O)(=O)C2CCCC2)=C1 PEZKCCUGBLAYSQ-UHFFFAOYSA-N 0.000 claims description 4
WWSBRQBNMHIVPT-UHFFFAOYSA-N 3-[4-[3-(2-cyclopentylacetyl)-4-hydroxyphenoxy]-3,5-dimethylanilino]-3-oxopropanoic acid Chemical compound CC1=CC(NC(=O)CC(O)=O)=CC(C)=C1OC1=CC=C(O)C(C(=O)CC2CCCC2)=C1 WWSBRQBNMHIVPT-UHFFFAOYSA-N 0.000 claims description 4
MQQNCVXXSUKWMM-UHFFFAOYSA-N 3-[3,5-dichloro-4-[3-(cyclobutylsulfamoyl)-4-hydroxyphenoxy]anilino]-3-oxopropanoic acid Chemical compound ClC1=CC(NC(=O)CC(=O)O)=CC(Cl)=C1OC1=CC=C(O)C(S(=O)(=O)NC2CCC2)=C1 MQQNCVXXSUKWMM-UHFFFAOYSA-N 0.000 claims description 3
XLJSSASFYOXSFG-UHFFFAOYSA-N 3-[3-chloro-4-[3-(4-fluorophenyl)sulfonyl-4-hydroxyphenoxy]-5-methylanilino]-2-methyl-3-oxopropanoic acid Chemical compound ClC1=CC(NC(=O)C(C(O)=O)C)=CC(C)=C1OC1=CC=C(O)C(S(=O)(=O)C=2C=CC(F)=CC=2)=C1 XLJSSASFYOXSFG-UHFFFAOYSA-N 0.000 claims description 3
PDUQTKAJACCACM-UHFFFAOYSA-N 3-[3-chloro-4-[3-(cyclopentylmethylsulfonyl)-4-hydroxyphenoxy]-5-methylanilino]-3-oxopropanoic acid Chemical compound CC1=CC(NC(=O)CC(O)=O)=CC(Cl)=C1OC1=CC=C(O)C(S(=O)(=O)CC2CCCC2)=C1 PDUQTKAJACCACM-UHFFFAOYSA-N 0.000 claims description 3
GHKUCWZCPWQVQJ-UHFFFAOYSA-N 3-[4-[3-[(4-fluorophenyl)-hydroxymethyl]-4-hydroxyphenoxy]-3,5-dimethylanilino]-3-oxopropanoic acid Chemical compound CC1=CC(NC(=O)CC(O)=O)=CC(C)=C1OC1=CC=C(O)C(C(O)C=2C=CC(F)=CC=2)=C1 GHKUCWZCPWQVQJ-UHFFFAOYSA-N 0.000 claims description 3
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 3
125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 2
ORVSYNSXGLXPKO-UHFFFAOYSA-N 3-[3-chloro-4-[3-(cyclobutylsulfamoyl)-4-hydroxyphenoxy]-5-methylanilino]-3-oxopropanoic acid Chemical compound CC1=CC(NC(=O)CC(O)=O)=CC(Cl)=C1OC1=CC=C(O)C(S(=O)(=O)NC2CCC2)=C1 ORVSYNSXGLXPKO-UHFFFAOYSA-N 0.000 claims description 2
DWXKQMXAPXMJLK-UHFFFAOYSA-N 3-[4-[3-(cyclobutylsulfamoyl)-4-hydroxyphenoxy]-3,5-dimethylanilino]-3-oxopropanoic acid Chemical compound CC1=CC(NC(=O)CC(O)=O)=CC(C)=C1OC1=CC=C(O)C(S(=O)(=O)NC2CCC2)=C1 DWXKQMXAPXMJLK-UHFFFAOYSA-N 0.000 claims description 2
VTKPWAHJASUHAQ-UHFFFAOYSA-N 3-[4-[3-(cyclopentylmethylsulfonyl)-4-hydroxyphenoxy]-3,5-dimethylanilino]-3-oxopropanoic acid Chemical compound CC1=CC(NC(=O)CC(O)=O)=CC(C)=C1OC1=CC=C(O)C(S(=O)(=O)CC2CCCC2)=C1 VTKPWAHJASUHAQ-UHFFFAOYSA-N 0.000 claims description 2
125000002877 alkyl aryl group Chemical group 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims 21
AKBBHCHDROZINA-UHFFFAOYSA-N 3-[3,5-dichloro-4-[3-(4-fluorophenyl)sulfonyl-4-hydroxyphenoxy]anilino]-3-oxopropanoic acid Chemical compound ClC1=CC(NC(=O)CC(=O)O)=CC(Cl)=C1OC1=CC=C(O)C(S(=O)(=O)C=2C=CC(F)=CC=2)=C1 AKBBHCHDROZINA-UHFFFAOYSA-N 0.000 claims 3
IEKHGQIKGADIPI-UHFFFAOYSA-N 3-[4-[3-(4-fluorophenyl)sulfonyl-4-hydroxyphenoxy]-3,5-dimethylanilino]-2-methyl-3-oxopropanoic acid Chemical compound CC1=CC(NC(=O)C(C(O)=O)C)=CC(C)=C1OC1=CC=C(O)C(S(=O)(=O)C=2C=CC(F)=CC=2)=C1 IEKHGQIKGADIPI-UHFFFAOYSA-N 0.000 claims 3
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125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 2
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SHDGIEFVTJYSQH-UHFFFAOYSA-N 3-amino-2-[3-chloro-4-[3-(4-fluorophenyl)sulfonyl-4-hydroxyphenoxy]-5-methylphenyl]-3-oxopropanoic acid Chemical compound CC1=CC(C(C(N)=O)C(O)=O)=CC(Cl)=C1OC1=CC=C(O)C(S(=O)(=O)C=2C=CC(F)=CC=2)=C1 SHDGIEFVTJYSQH-UHFFFAOYSA-N 0.000 claims 1
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 1
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
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- C07C235/72—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atoms of the carboxamide groups bound to acyclic carbon atoms
- C07C235/80—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atoms of the carboxamide groups bound to acyclic carbon atoms having carbon atoms of carboxamide groups and keto groups bound to the same carbon atom, e.g. acetoacetamides
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- C—CHEMISTRY; METALLURGY
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- C07C317/16—Sulfones; Sulfoxides having sulfone or sulfoxide groups and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C317/22—Sulfones; Sulfoxides having sulfone or sulfoxide groups and singly-bound oxygen atoms bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/46—Iso-indoles; Hydrogenated iso-indoles with an oxygen atom in position 1
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/04—Systems containing only non-condensed rings with a four-membered ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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Health & Medical Sciences (AREA)
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Bioinformatics & Cheminformatics (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Engineering & Computer Science (AREA)
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General Health & Medical Sciences (AREA)
Public Health (AREA)
Diabetes (AREA)
Endocrinology (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Hematology (AREA)
Obesity (AREA)
Physical Education & Sports Medicine (AREA)
Orthopedic Medicine & Surgery (AREA)
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Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

BG107036A 2000-03-31 2002-08-26 Малоhаmови киселини и техни производни като лиганди на тироидния рецептор BG107036A (bg)

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US19361800P	2000-03-31	2000-03-31
PCT/IB2001/000317 WO2001072692A1 (en)	2000-03-31	2001-03-07	Malonamic acids and derivatives thereof as thyroid receptor ligands

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US (1)	US20070173548A1 (et)
EP (1)	EP1268404B1 (et)
JP (1)	JP3866977B2 (et)
KR (1)	KR20020089420A (et)
CN (1)	CN1422246A (et)
AP (1)	AP2002002634A0 (et)
AR (1)	AR033516A1 (et)
AT (1)	ATE382602T1 (et)
AU (1)	AU2001237665A1 (et)
BG (1)	BG107036A (et)
BR (1)	BR0109625A (et)
CA (1)	CA2403902C (et)
CR (1)	CR6742A (et)
CZ (1)	CZ20023190A3 (et)
DE (1)	DE60132181D1 (et)
DZ (1)	DZ3276A1 (et)
EA (1)	EA200200921A1 (et)
EE (1)	EE200200566A (et)
GT (1)	GT200100041A (et)
HK (1)	HK1052498A1 (et)
HU (1)	HUP0300329A3 (et)
IL (1)	IL151376A0 (et)
IS (1)	IS6516A (et)
MA (1)	MA26886A1 (et)
MX (1)	MXPA02009702A (et)
NO (1)	NO20024639L (et)
NZ (1)	NZ520660A (et)
OA (1)	OA12237A (et)
PA (1)	PA8513801A1 (et)
PE (1)	PE20011186A1 (et)
PL (1)	PL358596A1 (et)
SK (1)	SK13762002A3 (et)
SV (1)	SV2002000357A (et)
TN (1)	TNSN01048A1 (et)
TR (1)	TR200202249T2 (et)
WO (1)	WO2001072692A1 (et)
YU (1)	YU74102A (et)
ZA (1)	ZA200207444B (et)

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2001
- 2001-03-07 HU HU0300329A patent/HUP0300329A3/hu unknown
- 2001-03-07 IL IL15137601A patent/IL151376A0/xx unknown
- 2001-03-07 OA OA1200200299A patent/OA12237A/en unknown
- 2001-03-07 EE EEP200200566A patent/EE200200566A/et unknown
- 2001-03-07 EA EA200200921A patent/EA200200921A1/ru unknown
- 2001-03-07 CA CA002403902A patent/CA2403902C/en not_active Expired - Fee Related
- 2001-03-07 AT AT01910082T patent/ATE382602T1/de not_active IP Right Cessation
- 2001-03-07 DZ DZ013276A patent/DZ3276A1/fr active
- 2001-03-07 CN CN01807559A patent/CN1422246A/zh active Pending
- 2001-03-07 TR TR2002/02249T patent/TR200202249T2/xx unknown
- 2001-03-07 BR BR0109625-7A patent/BR0109625A/pt not_active IP Right Cessation
- 2001-03-07 NZ NZ520660A patent/NZ520660A/en not_active Application Discontinuation
- 2001-03-07 AU AU2001237665A patent/AU2001237665A1/en not_active Abandoned
- 2001-03-07 WO PCT/IB2001/000317 patent/WO2001072692A1/en not_active Ceased
- 2001-03-07 DE DE60132181T patent/DE60132181D1/de not_active Expired - Lifetime
- 2001-03-07 MX MXPA02009702A patent/MXPA02009702A/es active IP Right Grant
- 2001-03-07 JP JP2001570607A patent/JP3866977B2/ja not_active Expired - Fee Related
- 2001-03-07 SK SK1376-2002A patent/SK13762002A3/sk not_active Application Discontinuation
- 2001-03-07 AP APAP/P/2002/002634A patent/AP2002002634A0/en unknown
- 2001-03-07 HK HK03104860.6A patent/HK1052498A1/zh unknown
- 2001-03-07 YU YU74102A patent/YU74102A/sh unknown
- 2001-03-07 PL PL01358596A patent/PL358596A1/xx not_active Application Discontinuation
- 2001-03-07 CZ CZ20023190A patent/CZ20023190A3/cs unknown
- 2001-03-07 KR KR1020027013044A patent/KR20020089420A/ko not_active Ceased
- 2001-03-07 EP EP01910082A patent/EP1268404B1/en not_active Expired - Lifetime
- 2001-03-16 PA PA20018513801A patent/PA8513801A1/es unknown
- 2001-03-19 GT GT200100041A patent/GT200100041A/es unknown
- 2001-03-28 PE PE2001000290A patent/PE20011186A1/es not_active Application Discontinuation
- 2001-03-29 AR ARP010101509A patent/AR033516A1/es unknown
- 2001-03-30 TN TNTNSN01048A patent/TNSN01048A1/fr unknown
- 2001-03-30 SV SV2001000357A patent/SV2002000357A/es not_active Application Discontinuation
2002
- 2002-08-21 IS IS6516A patent/IS6516A/is unknown
- 2002-08-26 BG BG107036A patent/BG107036A/bg unknown
- 2002-08-28 CR CR6742A patent/CR6742A/es not_active Application Discontinuation
- 2002-09-17 ZA ZA200207444A patent/ZA200207444B/en unknown
- 2002-09-24 MA MA26837A patent/MA26886A1/fr unknown
- 2002-09-27 NO NO20024639A patent/NO20024639L/no not_active Application Discontinuation
2007
- 2007-03-07 US US11/715,035 patent/US20070173548A1/en not_active Abandoned

Also Published As

Publication number	Publication date
AU2001237665A1 (en)	2001-10-08
DE60132181D1 (de)	2008-02-14
SV2002000357A (es)	2002-07-16
WO2001072692A1 (en)	2001-10-04
DZ3276A1 (fr)	2001-10-04
SK13762002A3 (sk)	2004-01-08
CN1422246A (zh)	2003-06-04
HUP0300329A2 (hu)	2003-07-28
NO20024639D0 (no)	2002-09-27
ZA200207444B (en)	2003-09-17
MXPA02009702A (es)	2003-03-27
OA12237A (en)	2003-10-23
US20070173548A1 (en)	2007-07-26
KR20020089420A (ko)	2002-11-29
TNSN01048A1 (fr)	2005-11-10
CR6742A (es)	2003-11-25
IL151376A0 (en)	2003-04-10
GT200100041A (es)	2002-03-22
EP1268404B1 (en)	2008-01-02
NO20024639L (no)	2002-09-27
ATE382602T1 (de)	2008-01-15
AP2002002634A0 (en)	2002-09-30
PE20011186A1 (es)	2001-11-15
HUP0300329A3 (en)	2004-08-30
JP3866977B2 (ja)	2007-01-10
IS6516A (is)	2002-08-21
AR033516A1 (es)	2003-12-26
PL358596A1 (en)	2004-08-09
EP1268404A1 (en)	2003-01-02
HK1052498A1 (zh)	2003-09-19
TR200202249T2 (tr)	2003-01-21
JP2003528847A (ja)	2003-09-30
MA26886A1 (fr)	2004-12-20
CA2403902A1 (en)	2001-10-04
EE200200566A (et)	2004-06-15
CZ20023190A3 (cs)	2003-10-15
YU74102A (sh)	2006-03-03
BR0109625A (pt)	2003-04-22
NZ520660A (en)	2004-03-26
PA8513801A1 (es)	2002-02-21
CA2403902C (en)	2007-04-24
EA200200921A1 (ru)	2003-02-27

Publication	Publication Date	Title
BG107036A (bg)	2003-04-30	Малоhаmови киселини и техни производни като лиганди на тироидния рецептор
US6924310B2 (en)	2005-08-02	Malonamic acids and derivatives thereof as thyroid receptor ligands
EP1148054B1 (en)	2005-11-23	Thyroid receptor ligands
EP1297833B1 (en)	2005-12-21	Indole carboxylic acids as thyroid receptor ligands
US6441015B2 (en)	2002-08-27	Tetrazole compounds as thyroid receptor ligands
US6620830B2 (en)	2003-09-16	Thyroid receptor ligands
US20050075377A1 (en)	2005-04-07	PPAR compounds
MXPA01004055A (en)	2002-06-05	Thyroid receptor ligands
JP2010511624A (ja)	2010-04-15	アテローム性動脈硬化および循環器疾患の治療のためのｃｅｔｐ阻害剤としてのｎ−（（３−ベンジル）−２，２−（ビス−フェニル）−プロパン−１−アミン誘導体