NZ526164A - Lactam compounds and pharmaceutical use for treating diabetes - Google Patents
Lactam compounds and pharmaceutical use for treating diabetesInfo
- Publication number
- NZ526164A NZ526164A NZ526164A NZ52616401A NZ526164A NZ 526164 A NZ526164 A NZ 526164A NZ 526164 A NZ526164 A NZ 526164A NZ 52616401 A NZ52616401 A NZ 52616401A NZ 526164 A NZ526164 A NZ 526164A
- Authority
- NZ
- New Zealand
- Prior art keywords
- group
- substituent
- groups
- ring
- compound
- Prior art date
Links
- -1 Lactam compounds Chemical class 0.000 title claims abstract description 194
- 206010012601 diabetes mellitus Diseases 0.000 title claims abstract description 15
- 150000003839 salts Chemical class 0.000 claims abstract description 27
- 239000004480 active ingredient Substances 0.000 claims abstract description 12
- 208000008589 Obesity Diseases 0.000 claims abstract description 9
- 208000007342 Diabetic Nephropathies Diseases 0.000 claims abstract description 8
- 206010063547 Diabetic macroangiopathy Diseases 0.000 claims abstract description 8
- 206010012689 Diabetic retinopathy Diseases 0.000 claims abstract description 8
- 208000033679 diabetic kidney disease Diseases 0.000 claims abstract description 8
- 208000032131 Diabetic Neuropathies Diseases 0.000 claims abstract description 7
- 150000001875 compounds Chemical class 0.000 claims description 168
- 125000001424 substituent group Chemical group 0.000 claims description 153
- 125000003118 aryl group Chemical group 0.000 claims description 56
- 125000000217 alkyl group Chemical group 0.000 claims description 49
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 47
- 125000002252 acyl group Chemical group 0.000 claims description 41
- 230000000694 effects Effects 0.000 claims description 34
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 33
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 32
- 125000004432 carbon atom Chemical group C* 0.000 claims description 32
- 125000003277 amino group Chemical group 0.000 claims description 28
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 27
- 125000005843 halogen group Chemical group 0.000 claims description 26
- 125000004423 acyloxy group Chemical group 0.000 claims description 25
- 125000003545 alkoxy group Chemical group 0.000 claims description 25
- 125000003282 alkyl amino group Chemical group 0.000 claims description 24
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 24
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 23
- 125000004414 alkyl thio group Chemical group 0.000 claims description 23
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 23
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 22
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 22
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 22
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 21
- 235000000346 sugar Nutrition 0.000 claims description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
- 125000000623 heterocyclic group Chemical group 0.000 claims description 16
- 239000003795 chemical substances by application Substances 0.000 claims description 15
- 125000001072 heteroaryl group Chemical group 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 13
- 239000008280 blood Substances 0.000 claims description 10
- 210000004369 blood Anatomy 0.000 claims description 10
- 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 10
- 125000001931 aliphatic group Chemical group 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 9
- 238000012360 testing method Methods 0.000 claims description 9
- 125000004104 aryloxy group Chemical group 0.000 claims description 8
- 208000002705 Glucose Intolerance Diseases 0.000 claims description 7
- 125000001769 aryl amino group Chemical group 0.000 claims description 7
- 125000003609 aryl vinyl group Chemical group 0.000 claims description 7
- 201000009104 prediabetes syndrome Diseases 0.000 claims description 7
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 125000000304 alkynyl group Chemical group 0.000 claims description 6
- 239000003472 antidiabetic agent Substances 0.000 claims description 5
- 229940126904 hypoglycaemic agent Drugs 0.000 claims description 5
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 4
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 4
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 4
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 4
- 241000699670 Mus sp. Species 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 229920000609 methyl cellulose Polymers 0.000 claims description 2
- 239000001923 methylcellulose Substances 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 239000000725 suspension Substances 0.000 claims description 2
- 125000002723 alicyclic group Chemical group 0.000 claims 5
- 125000004429 atom Chemical group 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 241000699666 Mus <mouse, genus> Species 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 229940068918 polyethylene glycol 400 Drugs 0.000 claims 1
- 210000003462 vein Anatomy 0.000 claims 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 abstract description 7
- 239000008103 glucose Substances 0.000 abstract description 7
- 239000003814 drug Substances 0.000 abstract description 5
- 229940079593 drug Drugs 0.000 abstract 1
- 235000020824 obesity Nutrition 0.000 abstract 1
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 94
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 54
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 48
- 238000005481 NMR spectroscopy Methods 0.000 description 45
- 238000000034 method Methods 0.000 description 43
- 239000000243 solution Substances 0.000 description 40
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
- 239000007858 starting material Substances 0.000 description 37
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 35
- 230000015572 biosynthetic process Effects 0.000 description 32
- 238000003786 synthesis reaction Methods 0.000 description 32
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- 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 description 24
- 150000001299 aldehydes Chemical class 0.000 description 23
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- 150000001923 cyclic compounds Chemical class 0.000 description 18
- 235000002639 sodium chloride Nutrition 0.000 description 17
- IUNJCFABHJZSKB-UHFFFAOYSA-N 2,4-dihydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C(O)=C1 IUNJCFABHJZSKB-UHFFFAOYSA-N 0.000 description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- 239000011541 reaction mixture Substances 0.000 description 15
- 238000005160 1H NMR spectroscopy Methods 0.000 description 14
- RUXHWBMJNBBYNL-UHFFFAOYSA-N 3-hydroxy-1,2-dihydropyrrol-5-one Chemical compound OC1=CC(=O)NC1 RUXHWBMJNBBYNL-UHFFFAOYSA-N 0.000 description 14
- 102100040996 Cochlin Human genes 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 101000748988 Homo sapiens Cochlin Proteins 0.000 description 14
- 239000007787 solid Substances 0.000 description 14
- 238000010898 silica gel chromatography Methods 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- 239000000126 substance Substances 0.000 description 13
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 12
- 102000004877 Insulin Human genes 0.000 description 12
- 108090001061 Insulin Proteins 0.000 description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- 229940125396 insulin Drugs 0.000 description 12
- 101150041968 CDC13 gene Proteins 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 11
- 238000001914 filtration Methods 0.000 description 11
- 239000000047 product Substances 0.000 description 11
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- 125000006165 cyclic alkyl group Chemical group 0.000 description 10
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- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- 238000000605 extraction Methods 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 239000000741 silica gel Substances 0.000 description 9
- 229910002027 silica gel Inorganic materials 0.000 description 9
- ZRYZBQLXDKPBDU-UHFFFAOYSA-N 4-bromobenzaldehyde Chemical compound BrC1=CC=C(C=O)C=C1 ZRYZBQLXDKPBDU-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 210000001789 adipocyte Anatomy 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 7
- 238000011156 evaluation Methods 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 238000004587 chromatography analysis Methods 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 239000013078 crystal Chemical group 0.000 description 6
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 6
- 238000005984 hydrogenation reaction Methods 0.000 description 6
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 125000000714 pyrimidinyl group Chemical group 0.000 description 6
- 230000003014 reinforcing effect Effects 0.000 description 6
- 238000004809 thin layer chromatography Methods 0.000 description 6
- 235000011054 acetic acid Nutrition 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 description 5
- 125000006239 protecting group Chemical group 0.000 description 5
- DOQJUNNMZNNQAD-UHFFFAOYSA-N pyrrolidine-2,4-dione Chemical compound O=C1CNC(=O)C1 DOQJUNNMZNNQAD-UHFFFAOYSA-N 0.000 description 5
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- NRKQMDLBMZFWDM-UHFFFAOYSA-N 4-tert-butyl-2-chlorobenzaldehyde Chemical compound CC(C)(C)C1=CC=C(C=O)C(Cl)=C1 NRKQMDLBMZFWDM-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
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- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed 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
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
- A61K31/551—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having two nitrogen atoms, e.g. dilazep
- A61K31/5513—1,4-Benzodiazepines, e.g. diazepam or clozapine
- A61K31/5517—1,4-Benzodiazepines, e.g. diazepam or clozapine condensed with five-membered rings having nitrogen as a ring hetero atom, e.g. imidazobenzodiazepines, triazolam
-
- 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
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
- A61K31/554—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having at least one nitrogen and one sulfur as ring hetero atoms, e.g. clothiapine, diltiazem
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—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
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
- C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
- C07D243/10—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Diabetes (AREA)
- Epidemiology (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Neurosurgery (AREA)
- Urology & Nephrology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Cardiology (AREA)
- Ophthalmology & Optometry (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Child & Adolescent Psychology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cephalosporin Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Hydrogenated Pyridines (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2000367175 | 2000-12-01 | ||
| PCT/JP2001/010435 WO2002044180A1 (en) | 2000-12-01 | 2001-11-29 | Lactam compounds and medicinal use thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ526164A true NZ526164A (en) | 2004-09-24 |
Family
ID=18837660
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ526164A NZ526164A (en) | 2000-12-01 | 2001-11-29 | Lactam compounds and pharmaceutical use for treating diabetes |
Country Status (26)
| Country | Link |
|---|---|
| US (3) | US7153850B2 (https=) |
| EP (1) | EP1346993B1 (https=) |
| JP (2) | JP3826400B2 (https=) |
| KR (1) | KR100826818B1 (https=) |
| CN (2) | CN100577651C (https=) |
| AT (1) | ATE446297T1 (https=) |
| AU (3) | AU1850202A (https=) |
| BG (1) | BG107857A (https=) |
| BR (1) | BR0115852A (https=) |
| CA (1) | CA2430124C (https=) |
| CZ (1) | CZ20031520A3 (https=) |
| DE (1) | DE60140270D1 (https=) |
| ES (1) | ES2331299T3 (https=) |
| HU (1) | HUP0400806A3 (https=) |
| IL (1) | IL156158A0 (https=) |
| MX (1) | MXPA03004876A (https=) |
| NO (1) | NO325401B1 (https=) |
| NZ (1) | NZ526164A (https=) |
| PL (1) | PL362835A1 (https=) |
| RU (1) | RU2287530C2 (https=) |
| SK (1) | SK6582003A3 (https=) |
| TW (1) | TWI241302B (https=) |
| UA (1) | UA76969C2 (https=) |
| WO (1) | WO2002044180A1 (https=) |
| YU (1) | YU42603A (https=) |
| ZA (1) | ZA200304100B (https=) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL362835A1 (en) * | 2000-12-01 | 2004-11-02 | Ajinomoto Co,Inc. | Lactam compounds and medicinal use thereof |
| CN1771040B (zh) * | 2003-02-07 | 2010-06-16 | 味之素株式会社 | 糖尿病治疗药 |
| CA2544310A1 (en) | 2003-10-31 | 2005-05-12 | Ajinomoto Co., Inc. | New fused polycyclic compounds having a heterocyclic ring(s) and pharmaceutical use thereof |
| JPWO2005068467A1 (ja) | 2004-01-14 | 2007-12-27 | 味の素株式会社 | 新規縮環化合物 |
| KR100858262B1 (ko) * | 2004-10-13 | 2008-09-11 | 에프. 호프만-라 로슈 아게 | Ｃｄｋ2 및 혈관신생에 대한 저해제로서 유용하고, 유방암,대장암, 폐암 및 전립선암의 치료용으로 유용한이중치환된 피라졸로벤조디아제핀 |
| NZ563131A (en) | 2005-04-28 | 2010-09-30 | Ajinomoto Kk | Tricyclic lactam compound as a hypoglycemic agent |
| EP2157092A4 (en) * | 2007-04-11 | 2011-04-13 | Ajinomoto Kk | Remedy for diabetes |
| WO2008139575A1 (ja) * | 2007-04-27 | 2008-11-20 | Ajinomoto Co., Inc. | 経口投与用製剤 |
| WO2008139574A1 (ja) * | 2007-04-27 | 2008-11-20 | Ajinomoto Co., Inc. | ラクタム化合物の結晶形およびその製造方法 |
| WO2008136392A1 (ja) * | 2007-04-27 | 2008-11-13 | Ajinomoto Co., Inc. | 経口投与用製剤 |
| CN101619041B (zh) * | 2008-07-02 | 2012-07-04 | 重庆华邦制药股份有限公司 | 一种二酮基含氮环化合物的合成方法及其中间体 |
| JP2012180282A (ja) * | 2009-07-02 | 2012-09-20 | Ajinomoto Co Inc | ラクタム化合物の製造方法およびその製造中間体 |
| JP2012180283A (ja) * | 2009-07-02 | 2012-09-20 | Ajinomoto Co Inc | ラクタム化合物の製造方法およびその製造中間体 |
| RU2017126027A (ru) * | 2014-12-22 | 2019-01-24 | ЕА Фарма Ко., Лтд. | Лекарственное средство для лечения расстройств эпителия роговицы |
| CA3011538A1 (en) | 2016-01-18 | 2017-07-27 | Arisan Therapeutics | Adamantane derivatives for the treatment of filovirus infection |
| WO2019018185A1 (en) | 2017-07-15 | 2019-01-24 | Arisan Therapeutics Inc. | ENANTIOMERICALLY PURE ADAMATANE DERIVATIVES FOR THE TREATMENT OF FILOVIRUS INFECTIONS |
| JP7566338B2 (ja) * | 2019-01-23 | 2024-10-15 | ▲たん▼解生醫股分有限公司 | グルコース代謝障害の長時間作用型の予防または治療に使用するためのβ－ラクタム化合物またはその塩 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US189597A (en) * | 1877-04-17 | Improvement in portable wash-stands | ||
| US48847A (en) * | 1865-07-18 | Improvement in vessels for reception and transportation of night-soil | ||
| GB8720414D0 (en) * | 1987-08-28 | 1987-10-07 | Roussel Lab Ltd | Chemical compounds |
| US5719296A (en) * | 1995-10-30 | 1998-02-17 | Merck & Co., Inc. | Pseudopeptide lactam inhibitors of peptide binding to MHC class II proteins |
| AU8592598A (en) | 1997-07-30 | 1999-02-22 | Wyeth | Tricyclic vasopressin agonists |
| JP4204657B2 (ja) | 1997-12-05 | 2009-01-07 | 有限会社ケムフィズ | 糖尿病の予防・治療剤 |
| PL362835A1 (en) * | 2000-12-01 | 2004-11-02 | Ajinomoto Co,Inc. | Lactam compounds and medicinal use thereof |
| CN1771040B (zh) * | 2003-02-07 | 2010-06-16 | 味之素株式会社 | 糖尿病治疗药 |
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2001
- 2001-11-29 PL PL01362835A patent/PL362835A1/xx not_active Application Discontinuation
- 2001-11-29 TW TW090129582A patent/TWI241302B/zh not_active IP Right Cessation
- 2001-11-29 RU RU2003116126/04A patent/RU2287530C2/ru not_active IP Right Cessation
- 2001-11-29 NZ NZ526164A patent/NZ526164A/en unknown
- 2001-11-29 CA CA2430124A patent/CA2430124C/en not_active Expired - Fee Related
- 2001-11-29 MX MXPA03004876A patent/MXPA03004876A/es active IP Right Grant
- 2001-11-29 HU HU0400806A patent/HUP0400806A3/hu unknown
- 2001-11-29 IL IL15615801A patent/IL156158A0/xx unknown
- 2001-11-29 YU YU42603A patent/YU42603A/sh unknown
- 2001-11-29 AT AT01998549T patent/ATE446297T1/de not_active IP Right Cessation
- 2001-11-29 DE DE60140270T patent/DE60140270D1/de not_active Expired - Lifetime
- 2001-11-29 AU AU1850202A patent/AU1850202A/xx active Pending
- 2001-11-29 WO PCT/JP2001/010435 patent/WO2002044180A1/ja not_active Ceased
- 2001-11-29 ES ES01998549T patent/ES2331299T3/es not_active Expired - Lifetime
- 2001-11-29 UA UA2003055026A patent/UA76969C2/uk unknown
- 2001-11-29 CN CN200610095903A patent/CN100577651C/zh not_active Expired - Fee Related
- 2001-11-29 CZ CZ20031520A patent/CZ20031520A3/cs unknown
- 2001-11-29 EP EP01998549A patent/EP1346993B1/en not_active Expired - Lifetime
- 2001-11-29 JP JP2002546550A patent/JP3826400B2/ja not_active Expired - Lifetime
- 2001-11-29 KR KR1020037007327A patent/KR100826818B1/ko not_active Expired - Fee Related
- 2001-11-29 AU AU2002218502A patent/AU2002218502B2/en not_active Ceased
- 2001-11-29 CN CNB018223559A patent/CN1269818C/zh not_active Expired - Fee Related
- 2001-11-29 BR BR0115852-0A patent/BR0115852A/pt not_active Application Discontinuation
- 2001-11-29 SK SK658-2003A patent/SK6582003A3/sk unknown
-
2003
- 2003-05-27 ZA ZA200304100A patent/ZA200304100B/en unknown
- 2003-05-28 NO NO20032439A patent/NO325401B1/no not_active IP Right Cessation
- 2003-05-29 BG BG107857A patent/BG107857A/bg unknown
- 2003-06-02 US US10/449,774 patent/US7153850B2/en not_active Expired - Fee Related
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2006
- 2006-04-06 US US11/398,675 patent/US7326701B2/en not_active Expired - Fee Related
- 2006-05-12 JP JP2006134026A patent/JP4505753B2/ja not_active Expired - Fee Related
- 2006-11-24 AU AU2006241377A patent/AU2006241377B2/en not_active Ceased
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2007
- 2007-11-30 US US11/948,288 patent/US7632830B2/en not_active Expired - Fee Related
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| PSEA | Patent sealed | ||
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