UA82867C2 - 2-pyridinecarboxamide derivatives - Google Patents

2-pyridinecarboxamide derivatives Download PDF

Info

Publication number: UA82867C2
Authority: UA; Ukraine
Prior art keywords: ylsulfanyl; group; pyridinecarboxamide; triazol; thiazol
Prior art date: 2003-02-13

Application number

UAA200508682A

Other languages

English (en)

Ukrainian (uk)

Original Assignee

Banyu Pharma Co Ltd

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.)

2003-02-13

Filing date

2004-02-13

Publication date

2008-05-26

2004-02-13 Application filed by Banyu Pharma Co Ltd filed Critical Banyu Pharma Co Ltd

2008-05-26 Publication of UA82867C2 publication Critical patent/UA82867C2/uk

Links

IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical class NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 title claims description 18
150000001875 compounds Chemical class 0.000 claims abstract description 510
125000000217 alkyl group Chemical group 0.000 claims abstract description 101
150000003839 salts Chemical class 0.000 claims abstract description 80
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 44
125000001072 heteroaryl group Chemical group 0.000 claims abstract description 34
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 26
229910052717 sulfur Inorganic materials 0.000 claims abstract description 20
206010012601 diabetes mellitus Diseases 0.000 claims abstract description 15
125000003118 aryl group Chemical group 0.000 claims abstract description 14
125000002619 bicyclic group Chemical group 0.000 claims abstract description 10
125000002950 monocyclic group Chemical group 0.000 claims abstract description 10
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 4
239000011593 sulfur Chemical group 0.000 claims abstract description 4
-1 carbamoyloxy group Chemical group 0.000 claims description 643
125000001424 substituent group Chemical group 0.000 claims description 47
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 43
108010021582 Glucokinase Proteins 0.000 claims description 38
102000030595 Glucokinase Human genes 0.000 claims description 36
125000003277 amino group Chemical group 0.000 claims description 32
125000005843 halogen group Chemical group 0.000 claims description 32
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 31
125000004432 carbon atom Chemical group C* 0.000 claims description 30
125000003545 alkoxy group Chemical group 0.000 claims description 28
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 25
125000004433 nitrogen atom Chemical group N* 0.000 claims description 24
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 20
239000003795 chemical substances by application Substances 0.000 claims description 18
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 17
125000004076 pyridyl group Chemical group 0.000 claims description 17
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 16
125000002252 acyl group Chemical group 0.000 claims description 16
125000004434 sulfur atom Chemical group 0.000 claims description 16
125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 14
125000004430 oxygen atom Chemical group O* 0.000 claims description 14
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
125000000335 thiazolyl group Chemical group 0.000 claims description 13
125000002883 imidazolyl group Chemical group 0.000 claims description 12
229930195734 saturated hydrocarbon Natural products 0.000 claims description 12
208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 12
125000000041 C6-C10 aryl group Chemical group 0.000 claims description 11
125000000842 isoxazolyl group Chemical group 0.000 claims description 11
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 11
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 10
125000004103 aminoalkyl group Chemical group 0.000 claims description 10
125000004093 cyano group Chemical group *C#N 0.000 claims description 10
NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 claims description 10
SWHGADZUKYCULK-UHFFFAOYSA-N 3-(1,3-thiazol-2-yl)pyridine-2-carboxamide Chemical compound NC(=O)C1=NC=CC=C1C1=NC=CS1 SWHGADZUKYCULK-UHFFFAOYSA-N 0.000 claims description 9
125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 9
150000003857 carboxamides Chemical class 0.000 claims description 9
125000000753 cycloalkyl group Chemical group 0.000 claims description 9
125000003226 pyrazolyl group Chemical group 0.000 claims description 9
125000001113 thiadiazolyl group Chemical group 0.000 claims description 9
125000001425 triazolyl group Chemical group 0.000 claims description 9
125000001786 isothiazolyl group Chemical group 0.000 claims description 8
125000002971 oxazolyl group Chemical group 0.000 claims description 8
125000000714 pyrimidinyl group Chemical group 0.000 claims description 8
230000001225 therapeutic effect Effects 0.000 claims description 8
125000001544 thienyl group Chemical group 0.000 claims description 8
238000009833 condensation Methods 0.000 claims description 7
230000005494 condensation Effects 0.000 claims description 7
125000004429 atom Chemical group 0.000 claims description 6
230000003914 insulin secretion Effects 0.000 claims description 6
230000000069 prophylactic effect Effects 0.000 claims description 6
125000003373 pyrazinyl group Chemical group 0.000 claims description 6
150000003852 triazoles Chemical class 0.000 claims description 6
102000004877 Insulin Human genes 0.000 claims description 5
108090001061 Insulin Proteins 0.000 claims description 5
208000008589 Obesity Diseases 0.000 claims description 5
YIKSCQDJHCMVMK-UHFFFAOYSA-N Oxamide Chemical compound NC(=O)C(N)=O YIKSCQDJHCMVMK-UHFFFAOYSA-N 0.000 claims description 5
239000000556 agonist Substances 0.000 claims description 5
125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 5
229910052799 carbon Inorganic materials 0.000 claims description 5
125000002541 furyl group Chemical group 0.000 claims description 5
125000005842 heteroatom Chemical group 0.000 claims description 5
229940125396 insulin Drugs 0.000 claims description 5
235000020824 obesity Nutrition 0.000 claims description 5
239000008194 pharmaceutical composition Substances 0.000 claims description 5
125000002098 pyridazinyl group Chemical group 0.000 claims description 5
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 4
125000005117 dialkylcarbamoyl group Chemical group 0.000 claims description 4
239000003937 drug carrier Substances 0.000 claims description 4
230000002265 prevention Effects 0.000 claims description 4
125000003831 tetrazolyl group Chemical group 0.000 claims description 4
JAGQJCICXSCFAM-UHFFFAOYSA-N 3-(4-fluorophenyl)sulfanyl-6-(1-methylimidazol-2-yl)sulfanyl-n-(4-methyl-1,3-thiazol-2-yl)pyridine-2-carboxamide Chemical compound CC1=CSC(NC(=O)C=2C(=CC=C(SC=3N(C=CN=3)C)N=2)SC=2C=CC(F)=CC=2)=N1 JAGQJCICXSCFAM-UHFFFAOYSA-N 0.000 claims description 3
102000005157 Somatostatin Human genes 0.000 claims description 3
108010056088 Somatostatin Proteins 0.000 claims description 3
125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 3
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 3
239000003112 inhibitor Substances 0.000 claims description 3
229910052751 metal Chemical group 0.000 claims description 3
239000002184 metal Chemical group 0.000 claims description 3
NHXLMOGPVYXJNR-ATOGVRKGSA-N somatostatin Chemical compound C([C@H]1C(=O)N[C@H](C(N[C@@H](CO)C(=O)N[C@@H](CSSC[C@@H](C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CC=2C3=CC=CC=C3NC=2)C(=O)N[C@@H](CCCCN)C(=O)N[C@H](C(=O)N1)[C@@H](C)O)NC(=O)CNC(=O)[C@H](C)N)C(O)=O)=O)[C@H](O)C)C1=CC=CC=C1 NHXLMOGPVYXJNR-ATOGVRKGSA-N 0.000 claims description 3
229960000553 somatostatin Drugs 0.000 claims description 3
KJTRXVXWSSPHRV-UHFFFAOYSA-N 4-benzoyl-5-methyl-2-phenyl-1h-pyrazol-3-one Chemical compound O=C1C(C(=O)C=2C=CC=CC=2)=C(C)NN1C1=CC=CC=C1 KJTRXVXWSSPHRV-UHFFFAOYSA-N 0.000 claims description 2
125000003368 amide group Chemical group 0.000 claims description 2
229940124828 glucokinase activator Drugs 0.000 claims description 2
125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims description 2
125000001183 hydrocarbyl group Chemical group 0.000 claims 2
NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims 1
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
238000012876 topography Methods 0.000 claims 1
108010045994 tricholysine Proteins 0.000 claims 1
229910052739 hydrogen Inorganic materials 0.000 abstract description 4
239000001257 hydrogen Substances 0.000 abstract description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 3
229910052760 oxygen Inorganic materials 0.000 abstract description 3
239000001301 oxygen Chemical group 0.000 abstract description 3
230000003213 activating effect Effects 0.000 abstract description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 1
238000002360 preparation method Methods 0.000 description 477
238000000034 method Methods 0.000 description 369
238000010561 standard procedure Methods 0.000 description 167
102100026933 Myelin-associated neurite-outgrowth inhibitor Human genes 0.000 description 155
238000006243 chemical reaction Methods 0.000 description 123
HUBANNPOLNYSAD-UHFFFAOYSA-N clopyralid Chemical compound OC(=O)C1=NC(Cl)=CC=C1Cl HUBANNPOLNYSAD-UHFFFAOYSA-N 0.000 description 121
238000005160 1H NMR spectroscopy Methods 0.000 description 104
239000000243 solution Substances 0.000 description 86
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 84
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 78
238000005481 NMR spectroscopy Methods 0.000 description 60
AFBBKYQYNPNMAT-UHFFFAOYSA-N 1h-1,2,4-triazol-1-ium-3-thiolate Chemical compound SC=1N=CNN=1 AFBBKYQYNPNMAT-UHFFFAOYSA-N 0.000 description 59
RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical compound NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 description 53
238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 47
229920006395 saturated elastomer Polymers 0.000 description 43
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 41
239000007864 aqueous solution Substances 0.000 description 39
239000002904 solvent Substances 0.000 description 36
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 35
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 32
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 30
238000002425 crystallisation Methods 0.000 description 29
230000008025 crystallization Effects 0.000 description 29
238000004587 chromatography analysis Methods 0.000 description 28
238000001226 reprecipitation Methods 0.000 description 27
238000000746 purification Methods 0.000 description 26
238000000638 solvent extraction Methods 0.000 description 26
238000005292 vacuum distillation Methods 0.000 description 26
150000001732 carboxylic acid derivatives Chemical class 0.000 description 25
239000007787 solid Substances 0.000 description 25
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 24
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NIFAOMSJMGEFTQ-UHFFFAOYSA-N 4-methoxybenzenethiol Chemical compound COC1=CC=C(S)C=C1 NIFAOMSJMGEFTQ-UHFFFAOYSA-N 0.000 description 21
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
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ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
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125000006239 protecting group Chemical group 0.000 description 20
229910000030 sodium bicarbonate Inorganic materials 0.000 description 20
235000017557 sodium bicarbonate Nutrition 0.000 description 20
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 18
OKIHXNKYYGUVTE-UHFFFAOYSA-N 4-Fluorothiophenol Chemical compound FC1=CC=C(S)C=C1 OKIHXNKYYGUVTE-UHFFFAOYSA-N 0.000 description 17
239000000126 substance Substances 0.000 description 16
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 15
230000035484 reaction time Effects 0.000 description 15
235000000346 sugar Nutrition 0.000 description 15
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 14
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VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
238000004440 column chromatography Methods 0.000 description 13
239000008103 glucose Substances 0.000 description 13
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 13
DJKUIGPCSNRFRK-UHFFFAOYSA-N 3-methyl-1,2,4-thiadiazol-5-amine Chemical compound CC1=NSC(N)=N1 DJKUIGPCSNRFRK-UHFFFAOYSA-N 0.000 description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
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WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
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239000004480 active ingredient Substances 0.000 description 12
229910052801 chlorine Inorganic materials 0.000 description 12
229910052731 fluorine Inorganic materials 0.000 description 12
150000002430 hydrocarbons Chemical group 0.000 description 12
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UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 12
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OUQMXTJYCAJLGO-UHFFFAOYSA-N 4-methyl-1,3-thiazol-2-amine Chemical compound CC1=CSC(N)=N1 OUQMXTJYCAJLGO-UHFFFAOYSA-N 0.000 description 9
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239000003513 alkali Substances 0.000 description 5
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- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
- 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
- A—HUMAN NECESSITIES
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- A61P13/12—Drugs for disorders of the urinary system of the kidneys
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A—HUMAN NECESSITIES
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- 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
- 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
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems

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Heart & Thoracic Surgery (AREA)
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Urology & Nephrology (AREA)
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UAA200508682A 2003-02-13 2004-02-13 2-pyridinecarboxamide derivatives UA82867C2 (en)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
JP2003034987		2003-02-13
JP2003342860		2003-10-01
JP2004014799		2004-01-22
PCT/JP2004/001568 WO2004081001A1 (ja)	2003-02-13	2004-02-13	新規２－ピリジンカルボキサミド誘導体

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UA82867C2 true UA82867C2 (en)	2008-05-26

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Application Number	Title	Priority Date	Filing Date
UAA200508682A UA82867C2 (en)	2003-02-13	2004-02-13	2-pyridinecarboxamide derivatives

Country Status (20)

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US (3)	US7629362B2 (de)
EP (1)	EP1598349B1 (de)
JP (1)	JP4400563B2 (de)
KR (1)	KR20050101208A (de)
AR (1)	AR045414A1 (de)
AT (1)	ATE517887T1 (de)
AU (2)	AU2004220234C1 (de)
BR (1)	BRPI0407283A (de)
CA (1)	CA2515841C (de)
EC (1)	ECSP056016A (de)
IL (1)	IL169905A0 (de)
MA (1)	MA27626A1 (de)
MX (1)	MXPA05008619A (de)
NO (1)	NO20054224L (de)
NZ (1)	NZ540791A (de)
PE (1)	PE20050194A1 (de)
TW (1)	TWI336329B (de)
UA (1)	UA82867C2 (de)
WO (1)	WO2004081001A1 (de)
ZA (1)	ZA200504852B (de)

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2005
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2009
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Publication number	Publication date
US8765789B2 (en)	2014-07-01
MXPA05008619A (es)	2005-11-04
KR20050101208A (ko)	2005-10-20
IL169905A0 (en)	2007-07-04
AU2004220234B2 (en)	2009-11-26
US20060258701A1 (en)	2006-11-16
EP1598349B1 (de)	2011-07-27
NO20054224D0 (no)	2005-09-12
TW200510381A (en)	2005-03-16
ATE517887T1 (de)	2011-08-15
ECSP056016A (es)	2006-01-27
NZ540791A (en)	2009-09-25
AR045414A1 (es)	2005-10-26
US7629362B2 (en)	2009-12-08
HK1088602A1 (zh)	2006-11-10
MA27626A1 (fr)	2005-11-01
NO20054224L (no)	2005-11-10
CA2515841C (en)	2010-06-01
US20100041660A1 (en)	2010-02-18
AU2004220234A1 (en)	2004-09-23
TWI336329B (en)	2011-01-21
US8344003B2 (en)	2013-01-01
PE20050194A1 (es)	2005-04-23
JPWO2004081001A1 (ja)	2006-06-08
AU2010200004B2 (en)	2012-07-19
US20130085156A1 (en)	2013-04-04
EP1598349A1 (de)	2005-11-23
EP1598349A4 (de)	2008-12-31
ZA200504852B (en)	2006-05-31
AU2004220234C1 (en)	2013-01-17
AU2010200004A1 (en)	2010-01-28
WO2004081001A1 (ja)	2004-09-23
BRPI0407283A (pt)	2006-01-31
CA2515841A1 (en)	2004-09-23
JP4400563B2 (ja)	2010-01-20

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