SA05260409B1 - مثبطات جديده لانزيمات البروتينات المعدنية لهيدانتوين - Google Patents
مثبطات جديده لانزيمات البروتينات المعدنية لهيدانتوين Download PDFInfo
- Publication number
- SA05260409B1 SA05260409B1 SA05260409A SA05260409A SA05260409B1 SA 05260409 B1 SA05260409 B1 SA 05260409B1 SA 05260409 A SA05260409 A SA 05260409A SA 05260409 A SA05260409 A SA 05260409A SA 05260409 B1 SA05260409 B1 SA 05260409B1
- Authority
- SA
- Saudi Arabia
- Prior art keywords
- formula
- compound
- methyl
- pharmaceutically acceptable
- acceptable salts
- Prior art date
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- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 title claims description 11
- 229940091173 hydantoin Drugs 0.000 title description 3
- 239000003475 metalloproteinase inhibitor Substances 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 99
- 238000011282 treatment Methods 0.000 claims abstract description 18
- 238000004519 manufacturing process Methods 0.000 claims abstract description 12
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 11
- 150000003839 salts Chemical class 0.000 claims description 44
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 30
- 102000004190 Enzymes Human genes 0.000 claims description 29
- 108090000790 Enzymes Proteins 0.000 claims description 29
- 201000010099 disease Diseases 0.000 claims description 28
- 238000006243 chemical reaction Methods 0.000 claims description 20
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 17
- 239000000126 substance Substances 0.000 claims description 14
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 13
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 229940079593 drug Drugs 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 208000006673 asthma Diseases 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 230000004224 protection Effects 0.000 claims description 7
- 206010028980 Neoplasm Diseases 0.000 claims description 6
- 239000003085 diluting agent Substances 0.000 claims description 6
- 201000006417 multiple sclerosis Diseases 0.000 claims description 6
- 201000008482 osteoarthritis Diseases 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 239000002671 adjuvant Substances 0.000 claims description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
- 239000001099 ammonium carbonate Substances 0.000 claims description 4
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 4
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 claims description 3
- 201000001320 Atherosclerosis Diseases 0.000 claims description 3
- 235000012501 ammonium carbonate Nutrition 0.000 claims description 3
- 201000011510 cancer Diseases 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 230000000414 obstructive effect Effects 0.000 claims description 3
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 claims description 3
- 238000006467 substitution reaction Methods 0.000 claims description 3
- 150000001642 boronic acid derivatives Chemical class 0.000 claims description 2
- 239000000470 constituent Substances 0.000 claims description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 230000001225 therapeutic effect Effects 0.000 claims description 2
- 101000577881 Homo sapiens Macrophage metalloelastase Proteins 0.000 claims 1
- 239000002131 composite material Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000001681 protective effect Effects 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 abstract description 22
- 102000002274 Matrix Metalloproteinases Human genes 0.000 abstract description 6
- 108010000684 Matrix Metalloproteinases Proteins 0.000 abstract description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 50
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 48
- 239000000243 solution Substances 0.000 description 36
- 239000000203 mixture Substances 0.000 description 35
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 32
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 32
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- 229940088598 enzyme Drugs 0.000 description 28
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- 238000000034 method Methods 0.000 description 25
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 23
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 22
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 21
- 235000019439 ethyl acetate Nutrition 0.000 description 19
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- 239000012074 organic phase Substances 0.000 description 17
- 239000000047 product Substances 0.000 description 17
- -1 1-fluoro-1-cyclopropyl Chemical group 0.000 description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- 239000000543 intermediate Substances 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
- 238000000746 purification Methods 0.000 description 14
- 239000007787 solid Substances 0.000 description 14
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- 230000005764 inhibitory process Effects 0.000 description 13
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- 102000005741 Metalloproteases Human genes 0.000 description 11
- 108010006035 Metalloproteases Proteins 0.000 description 11
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- 229910052786 argon Inorganic materials 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- 238000003786 synthesis reaction Methods 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- 230000003197 catalytic effect Effects 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 8
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 8
- 239000002585 base Substances 0.000 description 8
- 210000004027 cell Anatomy 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 239000012071 phase Substances 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 7
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 7
- 239000012043 crude product Substances 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 7
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
- 239000000758 substrate Substances 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 description 6
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 6
- OYNIUITTZQLGKT-UHFFFAOYSA-N 2-methoxy-4-methylpyridine-3-carbaldehyde Chemical compound COC1=NC=CC(C)=C1C=O OYNIUITTZQLGKT-UHFFFAOYSA-N 0.000 description 6
- 239000000872 buffer Substances 0.000 description 6
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 6
- 230000008569 process Effects 0.000 description 6
- 102000004169 proteins and genes Human genes 0.000 description 6
- 108090000623 proteins and genes Proteins 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 6
- OZTPQWRLHLQVBD-UHFFFAOYSA-N 1,2,3,4-tetrahydro-2,7-naphthyridine Chemical compound C1=NC=C2CNCCC2=C1 OZTPQWRLHLQVBD-UHFFFAOYSA-N 0.000 description 5
- 108060005980 Collagenase Proteins 0.000 description 5
- 102000029816 Collagenase Human genes 0.000 description 5
- 101000990902 Homo sapiens Matrix metalloproteinase-9 Proteins 0.000 description 5
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 5
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- 239000012298 atmosphere Substances 0.000 description 5
- 239000012267 brine Substances 0.000 description 5
- 239000003599 detergent Substances 0.000 description 5
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-Tetramethylpiperidine Substances CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 description 4
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 4
- ABRLVIWEDFKEOU-UHFFFAOYSA-N 6-(2-cyclopropylpyrimidin-5-yl)-1,2,3,4-tetrahydroisoquinoline Chemical compound C1CC1C1=NC=C(C=2C=C3CCNCC3=CC=2)C=N1 ABRLVIWEDFKEOU-UHFFFAOYSA-N 0.000 description 4
- WMLNKIRPHIHIAN-UHFFFAOYSA-N 6-methoxy-4-(2-trimethylsilylethynyl)pyridine-3-carbaldehyde Chemical compound COC1=CC(C#C[Si](C)(C)C)=C(C=O)C=N1 WMLNKIRPHIHIAN-UHFFFAOYSA-N 0.000 description 4
- 201000004624 Dermatitis Diseases 0.000 description 4
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
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- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical class CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
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- IPWKHHSGDUIRAH-UHFFFAOYSA-N bis(pinacolato)diboron Chemical compound O1C(C)(C)C(C)(C)OB1B1OC(C)(C)C(C)(C)O1 IPWKHHSGDUIRAH-UHFFFAOYSA-N 0.000 description 4
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
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- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 4
- AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 description 3
- UAMREVYOGWZBKV-UHFFFAOYSA-N 3-methoxy-2,7-naphthyridine Chemical compound C1=NC=C2C=NC(OC)=CC2=C1 UAMREVYOGWZBKV-UHFFFAOYSA-N 0.000 description 3
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- AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 description 3
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- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
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- 150000002576 ketones Chemical class 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
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- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 3
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- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical class ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 3
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- QUJWKZHUEPVGKJ-UHFFFAOYSA-N tert-butyl 6-(2-cyclopropylpyrimidin-5-yl)-3,4-dihydro-1h-isoquinoline-2-carboxylate Chemical compound C=1C=C2CN(C(=O)OC(C)(C)C)CCC2=CC=1C(C=N1)=CN=C1C1CC1 QUJWKZHUEPVGKJ-UHFFFAOYSA-N 0.000 description 3
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- GUEHESDOJBMSSE-UHFFFAOYSA-M (2-aminophenyl)mercury(1+);acetate Chemical compound CC(=O)O[Hg]C1=CC=CC=C1N GUEHESDOJBMSSE-UHFFFAOYSA-M 0.000 description 2
- XGNFHKACLYGNRB-UHFFFAOYSA-N (2-cyclopropylpyrimidin-4-yl)boronic acid Chemical compound OB(O)C1=CC=NC(C2CC2)=N1 XGNFHKACLYGNRB-UHFFFAOYSA-N 0.000 description 2
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- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 description 2
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- HCMMECMKVPHMDE-UHFFFAOYSA-N 2,7-naphthyridine Chemical compound C1=NC=C2C=NC=CC2=C1 HCMMECMKVPHMDE-UHFFFAOYSA-N 0.000 description 2
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- NZYNPWYIRBTOAV-UHFFFAOYSA-N 2-tert-butyl-6-(2-cyclopropylpyrimidin-5-yl)-3,4-dihydro-1h-2,7-naphthyridine Chemical compound N=1C=C2CN(C(C)(C)C)CCC2=CC=1C(C=N1)=CN=C1C1CC1 NZYNPWYIRBTOAV-UHFFFAOYSA-N 0.000 description 2
- ANURJXNEVQWODA-UHFFFAOYSA-N 5-bromo-2-cyclopropylpyrimidine Chemical compound N1=CC(Br)=CN=C1C1CC1 ANURJXNEVQWODA-UHFFFAOYSA-N 0.000 description 2
- YFUSZFNBTKHBIP-UHFFFAOYSA-N 6-(2-cyclopropylpyrimidin-5-yl)-1,2,3,4-tetrahydro-2,7-naphthyridine;hydrochloride Chemical compound Cl.C1CC1C1=NC=C(C=2N=CC=3CNCCC=3C=2)C=N1 YFUSZFNBTKHBIP-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- 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
- C07D401/14—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 three or more hetero rings
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- 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
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- 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
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- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
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- Neurology (AREA)
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- Immunology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
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| KR (1) | KR20070090924A (enExample) |
| CN (1) | CN101119987A (enExample) |
| AR (1) | AR051795A1 (enExample) |
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| AU (1) | AU2005317286B2 (enExample) |
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| CA (1) | CA2590845A1 (enExample) |
| ES (1) | ES2380670T3 (enExample) |
| IL (1) | IL183599A (enExample) |
| MX (1) | MX2007007023A (enExample) |
| MY (1) | MY147770A (enExample) |
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| RU (1) | RU2376301C2 (enExample) |
| SA (1) | SA05260409B1 (enExample) |
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| TW (1) | TW200635917A (enExample) |
| UA (1) | UA90285C2 (enExample) |
| WO (1) | WO2006065215A1 (enExample) |
| ZA (1) | ZA200705075B (enExample) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE0100902D0 (sv) * | 2001-03-15 | 2001-03-15 | Astrazeneca Ab | Compounds |
| SE0202539D0 (sv) | 2002-08-27 | 2002-08-27 | Astrazeneca Ab | Compounds |
| SE0401762D0 (sv) | 2004-07-05 | 2004-07-05 | Astrazeneca Ab | Novel compounds |
| US7648992B2 (en) * | 2004-07-05 | 2010-01-19 | Astrazeneca Ab | Hydantoin derivatives for the treatment of obstructive airway diseases |
| SE0403085D0 (sv) | 2004-12-17 | 2004-12-17 | Astrazeneca Ab | Novel componds |
| SE0403086D0 (sv) * | 2004-12-17 | 2004-12-17 | Astrazeneca Ab | Compounds |
| US7945626B2 (en) * | 2005-03-16 | 2011-05-17 | M&Fc Holding, Llc | Method, system, apparatus, and computer program product for determining a physical location of a sensor |
| JP5198256B2 (ja) * | 2005-05-04 | 2013-05-15 | エボテク エージー | 縮合複素環式化合物、並びにそれらの組成物及び使用 |
| TW200740769A (en) * | 2006-03-16 | 2007-11-01 | Astrazeneca Ab | Novel process |
| TW200831488A (en) * | 2006-11-29 | 2008-08-01 | Astrazeneca Ab | Novel compounds |
| KR101271219B1 (ko) * | 2011-01-27 | 2013-06-07 | 광주과학기술원 | 신규한 하이단토인 유도체 및 이의 용도 |
| ES2725881T3 (es) * | 2013-12-31 | 2019-09-30 | Ipsen Pharma Sas | Nuevos derivados de imidazolidin-2,4-diona |
| US20200268728A1 (en) | 2016-12-20 | 2020-08-27 | Sumitomo Dainippon Pharma Co., Ltd. | Drug targeting cancer stem cell |
| TWI901650B (zh) | 2020-03-26 | 2025-10-21 | 匈牙利商羅特格登公司 | 啶及吡啶并〔３，４－ｃ〕嗒衍生物 |
| US12649738B2 (en) | 2020-03-26 | 2026-06-09 | Richter Gedeon Nyrt. | 1,3-dihydro-2H-pyrrolo[3,4-c]pyridine derivatives as GABAA α5 receptor modulators |
| CN118748993A (zh) | 2021-12-28 | 2024-10-08 | 日本新药株式会社 | 吲唑化合物和药物 |
| US20260151410A1 (en) * | 2022-05-30 | 2026-06-04 | Scinnohub Pharmaceutical Co., Ltd | Tetrahydronaphthyridine Derivatives, Medicine Prepared Therefrom, and Applications Thereof in Preventing and Treating Adhesion-related Diseases |
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| SE0401763D0 (sv) | 2004-07-05 | 2004-07-05 | Astrazeneca Ab | Compounds |
| US7648992B2 (en) | 2004-07-05 | 2010-01-19 | Astrazeneca Ab | Hydantoin derivatives for the treatment of obstructive airway diseases |
| SE0403085D0 (sv) | 2004-12-17 | 2004-12-17 | Astrazeneca Ab | Novel componds |
| SE0403086D0 (sv) | 2004-12-17 | 2004-12-17 | Astrazeneca Ab | Compounds |
| TW200740769A (en) | 2006-03-16 | 2007-11-01 | Astrazeneca Ab | Novel process |
| TW200831488A (en) | 2006-11-29 | 2008-08-01 | Astrazeneca Ab | Novel compounds |
-
2004
- 2004-12-17 SE SE0403085A patent/SE0403085D0/sv unknown
-
2005
- 2005-12-14 EP EP05815745A patent/EP1831199B1/en not_active Expired - Lifetime
- 2005-12-14 NZ NZ555831A patent/NZ555831A/en not_active IP Right Cessation
- 2005-12-14 US US11/721,586 patent/US7655664B2/en not_active Expired - Fee Related
- 2005-12-14 CN CNA2005800481778A patent/CN101119987A/zh active Pending
- 2005-12-14 AU AU2005317286A patent/AU2005317286B2/en not_active Ceased
- 2005-12-14 CA CA002590845A patent/CA2590845A1/en not_active Abandoned
- 2005-12-14 RU RU2007126746/04A patent/RU2376301C2/ru not_active IP Right Cessation
- 2005-12-14 KR KR1020077013489A patent/KR20070090924A/ko not_active Ceased
- 2005-12-14 JP JP2007546609A patent/JP2008524210A/ja active Pending
- 2005-12-14 AT AT05815745T patent/ATE545642T1/de active
- 2005-12-14 ES ES05815745T patent/ES2380670T3/es not_active Expired - Lifetime
- 2005-12-14 BR BRPI0517035-4A patent/BRPI0517035A/pt not_active IP Right Cessation
- 2005-12-14 WO PCT/SE2005/001917 patent/WO2006065215A1/en not_active Ceased
- 2005-12-14 MX MX2007007023A patent/MX2007007023A/es active IP Right Grant
- 2005-12-14 UA UAA200706657A patent/UA90285C2/ru unknown
- 2005-12-15 AR ARP050105273A patent/AR051795A1/es not_active Application Discontinuation
- 2005-12-15 MY MYPI20055915A patent/MY147770A/en unknown
- 2005-12-16 TW TW094144602A patent/TW200635917A/zh unknown
- 2005-12-17 SA SA05260409A patent/SA05260409B1/ar unknown
-
2007
- 2007-05-31 IL IL183599A patent/IL183599A/en not_active IP Right Cessation
- 2007-06-12 ZA ZA200705075A patent/ZA200705075B/xx unknown
- 2007-07-10 NO NO20073572A patent/NO20073572L/no not_active Application Discontinuation
-
2010
- 2010-02-01 US US12/697,625 patent/US20100256166A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| US20080293743A1 (en) | 2008-11-27 |
| BRPI0517035A (pt) | 2008-09-30 |
| EP1831199B1 (en) | 2012-02-15 |
| MX2007007023A (es) | 2007-09-11 |
| CN101119987A (zh) | 2008-02-06 |
| NO20073572L (no) | 2007-09-12 |
| NZ555831A (en) | 2011-01-28 |
| UA90285C2 (ru) | 2010-04-26 |
| US7655664B2 (en) | 2010-02-02 |
| EP1831199A1 (en) | 2007-09-12 |
| KR20070090924A (ko) | 2007-09-06 |
| IL183599A0 (en) | 2007-09-20 |
| WO2006065215A1 (en) | 2006-06-22 |
| CA2590845A1 (en) | 2006-06-22 |
| AU2005317286B2 (en) | 2009-02-05 |
| ES2380670T3 (es) | 2012-05-17 |
| TW200635917A (en) | 2006-10-16 |
| JP2008524210A (ja) | 2008-07-10 |
| ZA200705075B (en) | 2008-12-31 |
| MY147770A (en) | 2013-01-31 |
| AR051795A1 (es) | 2007-02-07 |
| RU2007126746A (ru) | 2009-01-27 |
| ATE545642T1 (de) | 2012-03-15 |
| AU2005317286A1 (en) | 2006-06-22 |
| US20100256166A1 (en) | 2010-10-07 |
| SE0403085D0 (sv) | 2004-12-17 |
| RU2376301C2 (ru) | 2009-12-20 |
| IL183599A (en) | 2012-02-29 |
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