CA2554522A1 - 7-phenylamino-4-quinolone-3-carboxylic acid derivatives, methods for production and use thereof as medicaments - Google Patents
7-phenylamino-4-quinolone-3-carboxylic acid derivatives, methods for production and use thereof as medicaments Download PDFInfo
- Publication number
- CA2554522A1 CA2554522A1 CA002554522A CA2554522A CA2554522A1 CA 2554522 A1 CA2554522 A1 CA 2554522A1 CA 002554522 A CA002554522 A CA 002554522A CA 2554522 A CA2554522 A CA 2554522A CA 2554522 A1 CA2554522 A1 CA 2554522A1
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- Prior art keywords
- alkyl
- phenyl
- substituted
- iil
- iii
- Prior art date
- 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
Links
- 239000003814 drug Substances 0.000 title claims abstract 6
- UANVNDSRTZUBNX-UHFFFAOYSA-N 7-anilino-4-oxo-3h-quinoline-3-carboxylic acid Chemical class C=1C=C2C(=O)C(C(=O)O)C=NC2=CC=1NC1=CC=CC=C1 UANVNDSRTZUBNX-UHFFFAOYSA-N 0.000 title abstract 2
- 150000003839 salts Chemical class 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims abstract 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 31
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 13
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 7
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 4
- 239000004480 active ingredient Substances 0.000 claims 4
- 125000001072 heteroaryl group Chemical group 0.000 claims 4
- 125000004076 pyridyl group Chemical group 0.000 claims 4
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 2
- -1 N-((C1-C6)-alkyl)2 Chemical group 0.000 claims 2
- 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 claims 2
- 125000004404 heteroalkyl group Chemical group 0.000 claims 2
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 claims 1
- 230000003178 anti-diabetic effect Effects 0.000 claims 1
- 235000012000 cholesterol Nutrition 0.000 claims 1
- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 claims 1
- 230000002218 hypoglycaemic effect Effects 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 229940096701 plain lipid modifying drug hmg coa reductase inhibitors Drugs 0.000 claims 1
- 230000002265 prevention Effects 0.000 abstract 1
- 208000001072 type 2 diabetes mellitus Diseases 0.000 abstract 1
- 101150067539 AMBP gene Proteins 0.000 description 2
- 241000764238 Isis Species 0.000 description 2
- 241001514645 Agonis Species 0.000 description 1
- 101100000879 Caenorhabditis elegans actl-1 gene Proteins 0.000 description 1
- 241001327708 Coriaria sarmentosa Species 0.000 description 1
- 102100028203 Cytochrome c oxidase subunit 3 Human genes 0.000 description 1
- 101100020227 Danio rerio klhl31 gene Proteins 0.000 description 1
- 101100230385 Dickeya dadantii (strain 3937) celZ gene Proteins 0.000 description 1
- 241000255601 Drosophila melanogaster Species 0.000 description 1
- 101100289061 Drosophila melanogaster lili gene Proteins 0.000 description 1
- 101000861034 Homo sapiens Cytochrome c oxidase subunit 3 Proteins 0.000 description 1
- 101001043821 Homo sapiens Interleukin-31 Proteins 0.000 description 1
- 101000707770 Homo sapiens Splicing factor 3B subunit 2 Proteins 0.000 description 1
- 102100021596 Interleukin-31 Human genes 0.000 description 1
- 101100059652 Mus musculus Cetn1 gene Proteins 0.000 description 1
- 101100059655 Mus musculus Cetn2 gene Proteins 0.000 description 1
- 101100232411 Mus musculus Clns1a gene Proteins 0.000 description 1
- 101100020229 Mus musculus Klhl31 gene Proteins 0.000 description 1
- 101100235006 Mus musculus Lctl gene Proteins 0.000 description 1
- 101100034151 Mus musculus Rilp gene Proteins 0.000 description 1
- 239000004235 Orange GGN Substances 0.000 description 1
- 101100465037 Rattus norvegicus Prickle1 gene Proteins 0.000 description 1
- 102100031436 Splicing factor 3B subunit 2 Human genes 0.000 description 1
- CCAZWUJBLXKBAY-ULZPOIKGSA-N Tutin Chemical compound C([C@]12[C@@H]3O[C@@H]3[C@@]3(O)[C@H]4C(=O)O[C@@H]([C@H]([C@]32C)O)[C@H]4C(=C)C)O1 CCAZWUJBLXKBAY-ULZPOIKGSA-N 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 210000001699 lower leg Anatomy 0.000 description 1
- 101150020864 ltaS gene Proteins 0.000 description 1
- AHLBNYSZXLDEJQ-FWEHEUNISA-N orlistat Chemical compound CCCCCCCCCCC[C@H](OC(=O)[C@H](CC(C)C)NC=O)C[C@@H]1OC(=O)[C@H]1CCCCCC AHLBNYSZXLDEJQ-FWEHEUNISA-N 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 101150112339 ttrC gene Proteins 0.000 description 1
- 244000239635 ulla Species 0.000 description 1
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/576—Six-membered rings
- C07F9/60—Quinoline or hydrogenated quinoline ring systems
-
- 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
- A61K31/4709—Non-condensed quinolines and containing further heterocyclic rings
-
- 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
-
- 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
- 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
- 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
-
- 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
- C07D215/36—Sulfur atoms
-
- 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
- C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
-
- 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
- C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
- C07D215/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3 with oxygen atoms in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Diabetes (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Vascular Medicine (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Urology & Nephrology (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Quinoline Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
The invention relates to 7-phenylamino-4-quinolone-3-carboxylic acid derivatives, the physiologically-acceptable salts and physiologically-functional derivatives thereof, also compounds of formula (I), where the groups have the given meanings and the physiologically-acceptable salts thereof. Said compound are suitable for use, for example, as medicaments for the prevention and treatment of type 2 diabetes.
Description
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I~°ie aSCd ~:y eicotrc~tranSPort or iontoYiloresis aS tiescrbed, Col :~x~.?mple, iIz ~'llal-17~ I~.:a!i :-:~i :aearch, 2(f>): 3 i ~ ( 1 Wu).
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vli ~alltidia,betics mentioned in the Rote LiSte 2003, chapter 1?. ~ i~ey play he cozilbin<°t~ ~'.><'i~h ht: corllpounds of the formula I of the nvc~ntion in pal-ticular a,Jr a y~ler;istic ilnprov:_T:;~rlt of i~? tlvr t,~f'fect. Af?nlillistration of the active ill~redit;nt ccnlbination 11?ay take puce eitl~t;r ~~y :_~~;.lrate administration of the t~ctit'o, injredients to the patient or ill the ~Gml ;Jf cG l?oii-mtio;;
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:~:i~itors of ? av~~.T- ~n< ~.'n:es involved in tile Stimulation Gf g'ucs;nt:cge,nesiS and/or ;,i',' "~fJi°07ySIS, :'?IOt=i~,.l'~att'?1'S vi ail?COs::1?~3tdlCi:, C,Or11pO11iidS u't11C~1 lliCr il~id 1T12tal ~...J'~in, .;t'_~~.il a -aS !1t1~7;.%jWl~i1~31C1CLT?1C ?e.ti'.'e lil;=jT~;d12I1tS l3Tid ulltlhpldc:ll2i°" aCiiV<', Ln~'1'C~~LG.IaS, COf.tp~~:1'c'_~S
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I~°ie aSCd ~:y eicotrc~tranSPort or iontoYiloresis aS tiescrbed, Col :~x~.?mple, iIz ~'llal-17~ I~.:a!i :-:~i :aearch, 2(f>): 3 i ~ ( 1 Wu).
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vli ~alltidia,betics mentioned in the Rote LiSte 2003, chapter 1?. ~ i~ey play he cozilbin<°t~ ~'.><'i~h ht: corllpounds of the formula I of the nvc~ntion in pal-ticular a,Jr a y~ler;istic ilnprov:_T:;~rlt of i~? tlvr t,~f'fect. Af?nlillistration of the active ill~redit;nt ccnlbination 11?ay take puce eitl~t;r ~~y :_~~;.lrate administration of the t~ctit'o, injredients to the patient or ill the ~Gml ;Jf cG l?oii-mtio;;
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:~:i~itors of ? av~~.T- ~n< ~.'n:es involved in tile Stimulation Gf g'ucs;nt:cge,nesiS and/or ;,i',' "~fJi°07ySIS, :'?IOt=i~,.l'~att'?1'S vi ail?COs::1?~3tdlCi:, C,Or11pO11iidS u't11C~1 lliCr il~id 1T12tal ~...J'~in, .;t'_~~.il a -aS !1t1~7;.%jWl~i1~31C1CLT?1C ?e.ti'.'e lil;=jT~;d12I1tS l3Tid ulltlhpldc:ll2i°" aCiiV<', Ln~'1'C~~LG.IaS, COf.tp~~:1'c'_~S
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Claims
1. A compound of the formula I
in which the meanings are R1 OH, O-(C1-C6)-alkyl or O(C1-C6)-alkyl-OCO-(C1-C6)-alkyl;
R2 H, (C1-C6)-alkyl or phenyl;
R3 H, (C1-C3)-alkyl, (C3-C7)-cycloalkyl, pyridyl or phenyl, where alkyl may be substituted by R9 and where phenyl or pyridyl may be substituted by R10;
R9 NH2, NH-(C1-C6)-alkyl, N-((C1-C6)-alkyl)2, COOH, COO-(C1-C6)-alkyl, (C3-C7)-cycloalkyl, heteroalkyl, heteroaryl, O-phenyl or phenyl, where phenyl and heteroaryl may be substituted by R11;
R10 F, Cl, BR, (C1-C6-alkyl), O-(C1-C6)-alkyl, COOH, COO-(C1-C6)-alkyl, NH2, NH-(C1-C6)-alkyl or N((C1-C6)-alkyl)2;
R11 F, Cl, (C1-C6-alkyl), O-(C1-C6)-alkyl, NH2, NH-(C1-C6)-alkyl, N-((C1-C6)-alkyl)2 COOH or COO-C1-C4)-alkyl;
X C-R4 or N;
R4 H, F, Cl, BR, OH, NO2, CN, (C1-C6)-alkyl or O-(C1-C6)-alkyl, where alkyl may be substitutes more than once by F, Cl or Br;
R8 (C1-C3)-alkyl, (C3-C7)-cycloalkyl, pyridyl or phenyl, where alkyl may be substituted by R9 and where phenyl or pyridyl may be substituted by R10;
R9 NH2, NH-(C1-C6)-alkyl, N-((C1-C6)-alkyl)2, COOH, COO-(C1-C6)-alkyl, (C3-C7)-cycloalkyl, heteroalkyl, heteroaryl, O-phenyl or phenyl, where phenyl and heteroaryl may be substituted by R11;
R10 F, Cl, BR, (C1-C6-alkyl), O-(C1-C6)-alkyl, COOH, COO-(C1-C6)-alkyl, NH2, NH-(C1-C6)-alkyl or N((C1-C6)-alkyl)2;
R11 F, Cl, (C1-C6-alkyl), O-(C1-C6)-alkyl, NH2, NH-(C1-C6)-alkyl, N-((C1-C6)-alkyl)2 COOH or COO-C1-C4)-alkyl;
X C-R4 or N;
R4 H, F, Cl, BR, OH, NO2, CN, (C1-C6)-alkyl or O-(C1-C6)-alkyl, where alkyl may be substituted more than once by F, Cl or Br;
R5 H, F, Cl, BR, OH, NO2, CN, (C1-C6)-alkyl or O-(C1-C6)-alkyl, where alkyl may be substituted more than once by F, Cl or Br;
R1~OH, O-(C1-C6)-alkyl;~
R2~H;
R3~phenyl, where phenyl is substituted by R10;
R10~COOH, COO-(C1-C6)-alkyl;
X~C-R4;
R4~H(C1-C6)-alkyl;
R5~F,Cl, (C1-C6)-alkyl;
R6~H;
R7~H;
R8~phenyl, where phenyl is substituted one to five by F, Cl;
and the physiologically tolerated salts thereof.
5.~A compound as claimed in one or more of claims 1 to 4 for use as medicament.
6.~A medicament comprising one or more of the compounds as claimed in one ore more of claims 1 to 4.
7.~A medicament comprising one or more of the compounds as claimed in one or more of claims 1 to 4 and at least one other active ingredient.
8.~The medicament as claimed in claim 7, wherein the other active ingredient comprises one or more antidiabetics, hypoglycemic active ingredients, HMGCoA reductase inhibitors, cholesterol claimed in one or more of claims 1 to 4, which comprises mixing the active ingredient with a pharmaceutically suitable carrier and converting this mixture into a form suitable for administration.
in which the meanings are R1 OH, O-(C1-C6)-alkyl or O(C1-C6)-alkyl-OCO-(C1-C6)-alkyl;
R2 H, (C1-C6)-alkyl or phenyl;
R3 H, (C1-C3)-alkyl, (C3-C7)-cycloalkyl, pyridyl or phenyl, where alkyl may be substituted by R9 and where phenyl or pyridyl may be substituted by R10;
R9 NH2, NH-(C1-C6)-alkyl, N-((C1-C6)-alkyl)2, COOH, COO-(C1-C6)-alkyl, (C3-C7)-cycloalkyl, heteroalkyl, heteroaryl, O-phenyl or phenyl, where phenyl and heteroaryl may be substituted by R11;
R10 F, Cl, BR, (C1-C6-alkyl), O-(C1-C6)-alkyl, COOH, COO-(C1-C6)-alkyl, NH2, NH-(C1-C6)-alkyl or N((C1-C6)-alkyl)2;
R11 F, Cl, (C1-C6-alkyl), O-(C1-C6)-alkyl, NH2, NH-(C1-C6)-alkyl, N-((C1-C6)-alkyl)2 COOH or COO-C1-C4)-alkyl;
X C-R4 or N;
R4 H, F, Cl, BR, OH, NO2, CN, (C1-C6)-alkyl or O-(C1-C6)-alkyl, where alkyl may be substitutes more than once by F, Cl or Br;
R8 (C1-C3)-alkyl, (C3-C7)-cycloalkyl, pyridyl or phenyl, where alkyl may be substituted by R9 and where phenyl or pyridyl may be substituted by R10;
R9 NH2, NH-(C1-C6)-alkyl, N-((C1-C6)-alkyl)2, COOH, COO-(C1-C6)-alkyl, (C3-C7)-cycloalkyl, heteroalkyl, heteroaryl, O-phenyl or phenyl, where phenyl and heteroaryl may be substituted by R11;
R10 F, Cl, BR, (C1-C6-alkyl), O-(C1-C6)-alkyl, COOH, COO-(C1-C6)-alkyl, NH2, NH-(C1-C6)-alkyl or N((C1-C6)-alkyl)2;
R11 F, Cl, (C1-C6-alkyl), O-(C1-C6)-alkyl, NH2, NH-(C1-C6)-alkyl, N-((C1-C6)-alkyl)2 COOH or COO-C1-C4)-alkyl;
X C-R4 or N;
R4 H, F, Cl, BR, OH, NO2, CN, (C1-C6)-alkyl or O-(C1-C6)-alkyl, where alkyl may be substituted more than once by F, Cl or Br;
R5 H, F, Cl, BR, OH, NO2, CN, (C1-C6)-alkyl or O-(C1-C6)-alkyl, where alkyl may be substituted more than once by F, Cl or Br;
R1~OH, O-(C1-C6)-alkyl;~
R2~H;
R3~phenyl, where phenyl is substituted by R10;
R10~COOH, COO-(C1-C6)-alkyl;
X~C-R4;
R4~H(C1-C6)-alkyl;
R5~F,Cl, (C1-C6)-alkyl;
R6~H;
R7~H;
R8~phenyl, where phenyl is substituted one to five by F, Cl;
and the physiologically tolerated salts thereof.
5.~A compound as claimed in one or more of claims 1 to 4 for use as medicament.
6.~A medicament comprising one or more of the compounds as claimed in one ore more of claims 1 to 4.
7.~A medicament comprising one or more of the compounds as claimed in one or more of claims 1 to 4 and at least one other active ingredient.
8.~The medicament as claimed in claim 7, wherein the other active ingredient comprises one or more antidiabetics, hypoglycemic active ingredients, HMGCoA reductase inhibitors, cholesterol claimed in one or more of claims 1 to 4, which comprises mixing the active ingredient with a pharmaceutically suitable carrier and converting this mixture into a form suitable for administration.
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102004004973.4 | 2004-01-31 | ||
| DE102004004973A DE102004004973A1 (en) | 2004-01-31 | 2004-01-31 | New 7-phenylamino-quinolone or 1,8-naphthyridone derivatives, useful e.g. for treating type II diabetes or arteriosclerosis, are inhibitors of glycogen phosphorylase |
| DE102004033405.6 | 2004-07-10 | ||
| DE102004033405A DE102004033405A1 (en) | 2004-07-10 | 2004-07-10 | New 7-phenylamino-quinolone or 1,8-naphthyridone derivatives, useful e.g. for treating type II diabetes or arteriosclerosis, are inhibitors of glycogen phosphorylase |
| PCT/EP2005/000363 WO2005073229A1 (en) | 2004-01-31 | 2005-01-15 | 7-phenylamino-4-quinolone-3-carboxylic acid derivatives, methods for production and use thereof as medicaments |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2554522A1 true CA2554522A1 (en) | 2005-08-11 |
Family
ID=34828328
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002554522A Abandoned CA2554522A1 (en) | 2004-01-31 | 2005-01-15 | 7-phenylamino-4-quinolone-3-carboxylic acid derivatives, methods for production and use thereof as medicaments |
Country Status (19)
| Country | Link |
|---|---|
| EP (1) | EP1713803B1 (en) |
| JP (1) | JP2007519648A (en) |
| KR (1) | KR20060132671A (en) |
| AR (1) | AR047516A1 (en) |
| AT (1) | ATE438645T1 (en) |
| AU (1) | AU2005209365A1 (en) |
| BR (1) | BRPI0507309A (en) |
| CA (1) | CA2554522A1 (en) |
| DE (1) | DE502005007840D1 (en) |
| EC (1) | ECSP066734A (en) |
| IL (1) | IL176913A0 (en) |
| MA (1) | MA28337A1 (en) |
| OA (1) | OA13364A (en) |
| PA (1) | PA8622401A1 (en) |
| PE (1) | PE20051094A1 (en) |
| RU (1) | RU2006131306A (en) |
| TW (1) | TW200533353A (en) |
| UY (1) | UY28732A1 (en) |
| WO (1) | WO2005073229A1 (en) |
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| AU2006277682A1 (en) * | 2005-04-21 | 2007-02-15 | Targanta Therapeutics Inc. | Phosphonated fluoroquinolones, antibacterial analogs thereof, and methods for the prevention and treatment of bone and joint infections |
| KR20080048504A (en) | 2005-09-29 | 2008-06-02 | 사노피-아벤티스 | Phenyl- and pyridinyl-1,2,4-oxadiazolone derivatives, processes for their preparation and their use as pharmaceuticals |
| PE20110235A1 (en) | 2006-05-04 | 2011-04-14 | Boehringer Ingelheim Int | PHARMACEUTICAL COMBINATIONS INCLUDING LINAGLIPTIN AND METMORPHINE |
| RU2009108280A (en) | 2006-08-08 | 2010-09-20 | Санофи-Авентис (Fr) | Arylamino-arylalkyl-substituted imidazolidine-2,4-dione, methods for their preparation containing these compounds and their use |
| US10954231B2 (en) | 2006-10-16 | 2021-03-23 | Bionomics Limited | Anxiolytic compounds |
| JP5373613B2 (en) | 2006-10-16 | 2013-12-18 | バイオノミクス リミテッド | Novel anxiolytic compounds |
| DE102007005045B4 (en) | 2007-01-26 | 2008-12-18 | Sanofi-Aventis | Phenothiazine derivatives, process for their preparation and their use as medicines |
| EP2025674A1 (en) | 2007-08-15 | 2009-02-18 | sanofi-aventis | Substituted tetra hydro naphthalines, method for their manufacture and their use as drugs |
| AR072707A1 (en) | 2008-07-09 | 2010-09-15 | Sanofi Aventis | HETEROCICLIC COMPOUNDS, PROCESSES FOR THEIR PREPARATION, DRUGS THAT UNDERSTAND THESE COMPOUNDS AND THE USE OF THEM |
| WO2010073078A2 (en) * | 2008-12-22 | 2010-07-01 | Orchid Research Laboratories Ltd. | Heterocyclic compounds as hdac inhibitors |
| WO2011107494A1 (en) | 2010-03-03 | 2011-09-09 | Sanofi | Novel aromatic glycoside derivatives, medicaments containing said compounds, and the use thereof |
| EP2582709B1 (en) | 2010-06-18 | 2018-01-24 | Sanofi | Azolopyridin-3-one derivatives as inhibitors of lipases and phospholipases |
| US8530413B2 (en) | 2010-06-21 | 2013-09-10 | Sanofi | Heterocyclically substituted methoxyphenyl derivatives with an oxo group, processes for preparation thereof and use thereof as medicaments |
| TW201221505A (en) | 2010-07-05 | 2012-06-01 | Sanofi Sa | Aryloxyalkylene-substituted hydroxyphenylhexynoic acids, process for preparation thereof and use thereof as a medicament |
| TW201215387A (en) | 2010-07-05 | 2012-04-16 | Sanofi Aventis | Spirocyclically substituted 1,3-propane dioxide derivatives, processes for preparation thereof and use thereof as a medicament |
| TW201215388A (en) | 2010-07-05 | 2012-04-16 | Sanofi Sa | (2-aryloxyacetylamino)phenylpropionic acid derivatives, processes for preparation thereof and use thereof as medicaments |
| US9023848B2 (en) | 2011-03-02 | 2015-05-05 | Bionomics Limited | Small-molecules as therapeutics |
| EP2683702B1 (en) | 2011-03-08 | 2014-12-24 | Sanofi | New substituted phenyl oxathiazine derivatives, method for their manufacture, medicines containing these compounds and their application |
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| US8846666B2 (en) | 2011-03-08 | 2014-09-30 | Sanofi | Oxathiazine derivatives which are substituted with benzyl or heteromethylene groups, method for producing them, their use as medicine and drug containing said derivatives and the use thereof |
| US8710050B2 (en) | 2011-03-08 | 2014-04-29 | Sanofi | Di and tri- substituted oxathiazine derivatives, method for the production, method for the production thereof, use thereof as medicine and drug containing said derivatives and use thereof |
| EP2766349B1 (en) | 2011-03-08 | 2016-06-01 | Sanofi | Oxathiazine derivatives substituted with carbocycles or heterocycles, method for producing same, drugs containing said compounds, and use thereof |
| EP2683698B1 (en) | 2011-03-08 | 2017-10-04 | Sanofi | Benzyl-oxathiazine derivates substituted with adamantane or noradamantane, medicaments containing said compounds and use thereof |
| EP2683703B1 (en) | 2011-03-08 | 2015-05-27 | Sanofi | Novel substituted phenyl-oxathiazine derivatives, method for producing them, drugs containing said compounds and the use thereof |
| US8828995B2 (en) | 2011-03-08 | 2014-09-09 | Sanofi | Branched oxathiazine derivatives, method for the production thereof, use thereof as medicine and drug containing said derivatives and use thereof |
| WO2012151640A1 (en) | 2011-05-12 | 2012-11-15 | Bionomics Limited | Methods for preparing naphthyridines |
| EP2567959B1 (en) | 2011-09-12 | 2014-04-16 | Sanofi | 6-(4-hydroxy-phenyl)-3-styryl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| WO2013037390A1 (en) | 2011-09-12 | 2013-03-21 | Sanofi | 6-(4-hydroxy-phenyl)-3-styryl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| EP2760862B1 (en) | 2011-09-27 | 2015-10-21 | Sanofi | 6-(4-hydroxy-phenyl)-3-alkyl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0205165D0 (en) * | 2002-03-06 | 2002-04-17 | Astrazeneca Ab | Chemical compounds |
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2005
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- 2005-01-15 AT AT05700953T patent/ATE438645T1/en not_active IP Right Cessation
- 2005-01-15 CA CA002554522A patent/CA2554522A1/en not_active Abandoned
- 2005-01-15 OA OA1200600243A patent/OA13364A/en unknown
- 2005-01-15 RU RU2006131306/04A patent/RU2006131306A/en unknown
- 2005-01-15 WO PCT/EP2005/000363 patent/WO2005073229A1/en active Application Filing
- 2005-01-15 KR KR1020067015355A patent/KR20060132671A/en not_active Application Discontinuation
- 2005-01-15 EP EP05700953A patent/EP1713803B1/en active Active
- 2005-01-15 AU AU2005209365A patent/AU2005209365A1/en not_active Abandoned
- 2005-01-15 JP JP2006549988A patent/JP2007519648A/en not_active Abandoned
- 2005-01-15 BR BRPI0507309-0A patent/BRPI0507309A/en not_active Application Discontinuation
- 2005-01-27 TW TW094102386A patent/TW200533353A/en unknown
- 2005-01-28 AR ARP050100321A patent/AR047516A1/en unknown
- 2005-01-28 PE PE2005000109A patent/PE20051094A1/en not_active Application Discontinuation
- 2005-01-31 PA PA20058622401A patent/PA8622401A1/en unknown
- 2005-01-31 UY UY28732A patent/UY28732A1/en unknown
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2006
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- 2006-07-28 MA MA29216A patent/MA28337A1/en unknown
- 2006-07-28 EC EC2006006734A patent/ECSP066734A/en unknown
Also Published As
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|---|---|
| EP1713803B1 (en) | 2009-08-05 |
| TW200533353A (en) | 2005-10-16 |
| JP2007519648A (en) | 2007-07-19 |
| AR047516A1 (en) | 2006-01-25 |
| IL176913A0 (en) | 2006-12-10 |
| PA8622401A1 (en) | 2005-08-10 |
| OA13364A (en) | 2007-04-13 |
| EP1713803A1 (en) | 2006-10-25 |
| UY28732A1 (en) | 2005-08-31 |
| DE502005007840D1 (en) | 2009-09-17 |
| MA28337A1 (en) | 2006-12-01 |
| BRPI0507309A (en) | 2007-06-26 |
| ATE438645T1 (en) | 2009-08-15 |
| ECSP066734A (en) | 2006-10-31 |
| WO2005073229A1 (en) | 2005-08-11 |
| AU2005209365A1 (en) | 2005-08-11 |
| KR20060132671A (en) | 2006-12-21 |
| RU2006131306A (en) | 2008-03-10 |
| PE20051094A1 (en) | 2006-02-07 |
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