KR20050105443A - 신규한 치환된 2,3-벤조디아제핀 유도체 - Google Patents
신규한 치환된 2,3-벤조디아제핀 유도체 Download PDFInfo
- Publication number
- KR20050105443A KR20050105443A KR1020057013696A KR20057013696A KR20050105443A KR 20050105443 A KR20050105443 A KR 20050105443A KR 1020057013696 A KR1020057013696 A KR 1020057013696A KR 20057013696 A KR20057013696 A KR 20057013696A KR 20050105443 A KR20050105443 A KR 20050105443A
- Authority
- KR
- South Korea
- Prior art keywords
- methyl
- compound
- dihydro
- benzodiazepine
- group
- 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.)
- Withdrawn
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- RPBDCDQMCRHNLM-UHFFFAOYSA-N C1=NNC=C2C=CC=CC2=C1 Chemical class C1=NNC=C2C=CC=CC2=C1 RPBDCDQMCRHNLM-UHFFFAOYSA-N 0.000 title claims abstract description 150
- 238000000034 method Methods 0.000 claims abstract description 120
- 239000002253 acid Substances 0.000 claims abstract description 28
- 150000003839 salts Chemical class 0.000 claims abstract description 23
- 230000001154 acute effect Effects 0.000 claims abstract description 20
- 206010015037 epilepsy Diseases 0.000 claims abstract description 15
- 208000015122 neurodegenerative disease Diseases 0.000 claims abstract description 11
- 230000001684 chronic effect Effects 0.000 claims abstract description 10
- 230000004770 neurodegeneration Effects 0.000 claims abstract description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 9
- 208000007101 Muscle Cramp Diseases 0.000 claims abstract description 7
- 208000037976 chronic inflammation Diseases 0.000 claims abstract description 6
- 208000037893 chronic inflammatory disorder Diseases 0.000 claims abstract description 6
- 150000001875 compounds Chemical class 0.000 claims description 298
- -1 cyanomethyl group Chemical group 0.000 claims description 101
- 241000124008 Mammalia Species 0.000 claims description 20
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims description 16
- 229940049706 benzodiazepine Drugs 0.000 claims description 16
- 229930195712 glutamate Natural products 0.000 claims description 16
- 125000003277 amino group Chemical group 0.000 claims description 14
- 125000005843 halogen group Chemical group 0.000 claims description 13
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 11
- 201000010099 disease Diseases 0.000 claims description 9
- 125000005842 heteroatom Chemical group 0.000 claims description 9
- SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 claims description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 206010021118 Hypotonia Diseases 0.000 claims description 8
- 201000006417 multiple sclerosis Diseases 0.000 claims description 8
- 230000036640 muscle relaxation Effects 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 208000005392 Spasm Diseases 0.000 claims description 7
- 210000004556 brain Anatomy 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 208000027866 inflammatory disease Diseases 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000004429 atom Chemical group 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 229920006395 saturated elastomer Polymers 0.000 claims description 6
- 208000030507 AIDS Diseases 0.000 claims description 5
- 208000018737 Parkinson disease Diseases 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 206010006451 bronchitis Diseases 0.000 claims description 5
- 230000004064 dysfunction Effects 0.000 claims description 5
- 230000001575 pathological effect Effects 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 4
- DZISRJWEOMPAIL-ISZGNANSSA-N 2-methyl-4-[(8r)-8-methyl-7-[5-[(e)-prop-1-enyl]-1,3,4-thiadiazol-2-yl]-8,9-dihydro-[1,3]dioxolo[4,5-h][2,3]benzodiazepin-5-yl]aniline Chemical compound S1C(/C=C/C)=NN=C1N1[C@H](C)CC2=CC(OCO3)=C3C=C2C(C=2C=C(C)C(N)=CC=2)=N1 DZISRJWEOMPAIL-ISZGNANSSA-N 0.000 claims description 4
- 208000024827 Alzheimer disease Diseases 0.000 claims description 4
- 201000006474 Brain Ischemia Diseases 0.000 claims description 4
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- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
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- 206010008118 cerebral infarction Diseases 0.000 claims description 4
- 230000036407 pain Effects 0.000 claims description 4
- UGUHFDPGDQDVGX-UHFFFAOYSA-N 1,2,3-thiadiazole Chemical compound C1=CSN=N1 UGUHFDPGDQDVGX-UHFFFAOYSA-N 0.000 claims description 3
- FKASFBLJDCHBNZ-UHFFFAOYSA-N 1,3,4-oxadiazole Chemical compound C1=NN=CO1 FKASFBLJDCHBNZ-UHFFFAOYSA-N 0.000 claims description 3
- MBIZXFATKUQOOA-UHFFFAOYSA-N 1,3,4-thiadiazole Chemical compound C1=NN=CS1 MBIZXFATKUQOOA-UHFFFAOYSA-N 0.000 claims description 3
- CPDCZSIMXFZSGX-SNVBAGLBSA-N 2-chloro-4-[(8r)-8-methyl-7-(5-methyl-1,3,4-thiadiazol-2-yl)-8,9-dihydro-[1,3]dioxolo[4,5-h][2,3]benzodiazepin-5-yl]aniline Chemical compound C([C@H]1C)C2=CC=3OCOC=3C=C2C(C=2C=C(Cl)C(N)=CC=2)=NN1C1=NN=C(C)S1 CPDCZSIMXFZSGX-SNVBAGLBSA-N 0.000 claims description 3
- HCOJNYUPUOBYDH-GFCCVEGCSA-N 2-methyl-4-[(8r)-8-methyl-7-(1,3,4-thiadiazol-2-yl)-8,9-dihydro-[1,3]dioxolo[4,5-h][2,3]benzodiazepin-5-yl]aniline Chemical compound C([C@H]1C)C2=CC=3OCOC=3C=C2C(C=2C=C(C)C(N)=CC=2)=NN1C1=NN=CS1 HCOJNYUPUOBYDH-GFCCVEGCSA-N 0.000 claims description 3
- DBDUGNPURSLMPS-GFCCVEGCSA-N 2-methyl-4-[(8r)-8-methyl-7-(5-methyl-1,3,4-thiadiazol-2-yl)-8,9-dihydro-[1,3]dioxolo[4,5-h][2,3]benzodiazepin-5-yl]aniline Chemical compound C([C@H]1C)C2=CC=3OCOC=3C=C2C(C=2C=C(C)C(N)=CC=2)=NN1C1=NN=C(C)S1 DBDUGNPURSLMPS-GFCCVEGCSA-N 0.000 claims description 3
- ZMKBCJHGTFWHJI-GFCCVEGCSA-N 4-[(8r)-7-(4,5-dihydro-1,3-thiazol-2-yl)-8-methyl-8,9-dihydro-[1,3]dioxolo[4,5-h][2,3]benzodiazepin-5-yl]aniline Chemical class C([C@H]1C)C2=CC=3OCOC=3C=C2C(C=2C=CC(N)=CC=2)=NN1C1=NCCS1 ZMKBCJHGTFWHJI-GFCCVEGCSA-N 0.000 claims description 3
- OTLOBZLSZJVQQA-CYBMUJFWSA-N 4-[(8r)-7-(5-ethyl-1,3,4-thiadiazol-2-yl)-8-methyl-8,9-dihydro-[1,3]dioxolo[4,5-h][2,3]benzodiazepin-5-yl]-2-methylaniline Chemical compound S1C(CC)=NN=C1N1[C@H](C)CC2=CC(OCO3)=C3C=C2C(C=2C=C(C)C(N)=CC=2)=N1 OTLOBZLSZJVQQA-CYBMUJFWSA-N 0.000 claims description 3
- JRXDNQCAOCOIGM-GFCCVEGCSA-N 4-[(8r)-7-(5-ethyl-1,3,4-thiadiazol-2-yl)-8-methyl-8,9-dihydro-[1,3]dioxolo[4,5-h][2,3]benzodiazepin-5-yl]aniline Chemical compound S1C(CC)=NN=C1N1[C@H](C)CC2=CC(OCO3)=C3C=C2C(C=2C=CC(N)=CC=2)=N1 JRXDNQCAOCOIGM-GFCCVEGCSA-N 0.000 claims description 3
- AQVHOPUVJNUMRK-LLVKDONJSA-N 4-[(8r)-8-methyl-7-(1,3,4-thiadiazol-2-yl)-8,9-dihydro-[1,3]dioxolo[4,5-h][2,3]benzodiazepin-5-yl]aniline Chemical class C([C@H]1C)C2=CC=3OCOC=3C=C2C(C=2C=CC(N)=CC=2)=NN1C1=NN=CS1 AQVHOPUVJNUMRK-LLVKDONJSA-N 0.000 claims description 3
- CUFZAXVDJYYCST-GFCCVEGCSA-N 4-[(8r)-8-methyl-7-(1,3-thiazol-2-yl)-8,9-dihydro-[1,3]dioxolo[4,5-h][2,3]benzodiazepin-5-yl]aniline Chemical compound C([C@H]1C)C2=CC=3OCOC=3C=C2C(C=2C=CC(N)=CC=2)=NN1C1=NC=CS1 CUFZAXVDJYYCST-GFCCVEGCSA-N 0.000 claims description 3
- CNJBMCKQTBPYCD-LLVKDONJSA-N 4-[(8r)-8-methyl-7-(5-methyl-1,3,4-oxadiazol-2-yl)-8,9-dihydro-[1,3]dioxolo[4,5-h][2,3]benzodiazepin-5-yl]aniline Chemical compound C([C@H]1C)C2=CC=3OCOC=3C=C2C(C=2C=CC(N)=CC=2)=NN1C1=NN=C(C)O1 CNJBMCKQTBPYCD-LLVKDONJSA-N 0.000 claims description 3
- SGQFSRKCDSMQQY-LLVKDONJSA-N 4-[(8r)-8-methyl-7-(5-methyl-1,3,4-thiadiazol-2-yl)-8,9-dihydro-[1,3]dioxolo[4,5-h][2,3]benzodiazepin-5-yl]aniline Chemical compound C([C@H]1C)C2=CC=3OCOC=3C=C2C(C=2C=CC(N)=CC=2)=NN1C1=NN=C(C)S1 SGQFSRKCDSMQQY-LLVKDONJSA-N 0.000 claims description 3
- 206010012689 Diabetic retinopathy Diseases 0.000 claims description 3
- 208000010412 Glaucoma Diseases 0.000 claims description 3
- 206010021639 Incontinence Diseases 0.000 claims description 3
- 230000000172 allergic effect Effects 0.000 claims description 3
- 230000003556 anti-epileptic effect Effects 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 208000010668 atopic eczema Diseases 0.000 claims description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 201000006517 essential tremor Diseases 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 208000020431 spinal cord injury Diseases 0.000 claims description 3
- OGVWWGVZVJUPHF-UHFFFAOYSA-N 1,2,4-thiadiazol-3-one Chemical compound O=C1N=CSN1 OGVWWGVZVJUPHF-UHFFFAOYSA-N 0.000 claims description 2
- CEBAFUFWRQAHJL-UHFFFAOYSA-N 1,4,2-oxathiazole Chemical compound C1ON=CS1 CEBAFUFWRQAHJL-UHFFFAOYSA-N 0.000 claims description 2
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 claims description 2
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 claims description 2
- OBQQXJNPNJYUKU-UHFFFAOYSA-N 2h-1,3,4-thiadiazol-5-one Chemical compound O=C1SCN=N1 OBQQXJNPNJYUKU-UHFFFAOYSA-N 0.000 claims description 2
- CZWWCTHQXBMHDA-UHFFFAOYSA-N 3h-1,3-thiazol-2-one Chemical compound OC1=NC=CS1 CZWWCTHQXBMHDA-UHFFFAOYSA-N 0.000 claims description 2
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims description 2
- 206010006458 Bronchitis chronic Diseases 0.000 claims description 2
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 2
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 2
- 206010039085 Rhinitis allergic Diseases 0.000 claims description 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 2
- 201000010105 allergic rhinitis Diseases 0.000 claims description 2
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 208000007451 chronic bronchitis Diseases 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
- 208000030603 inherited susceptibility to asthma Diseases 0.000 claims description 2
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims description 2
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- 150000003536 tetrazoles Chemical class 0.000 claims description 2
- YGNGABUJMXJPIJ-UHFFFAOYSA-N thiatriazole Chemical compound C1=NN=NS1 YGNGABUJMXJPIJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 125000004521 1,3,4-thiadiazol-2-yl group Chemical group S1C(=NN=C1)* 0.000 claims 2
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- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims 1
- QBZMIFMKDXUHIR-NFKWMPFVSA-N C[C@H](C1)N(C2=NN=C(OC)[S+]2C)N=C(C(C=C2)=CC(Cl)=C2N)C2=C1C=C1OCOC1=C2 Chemical compound C[C@H](C1)N(C2=NN=C(OC)[S+]2C)N=C(C(C=C2)=CC(Cl)=C2N)C2=C1C=C1OCOC1=C2 QBZMIFMKDXUHIR-NFKWMPFVSA-N 0.000 claims 1
- 230000003110 anti-inflammatory effect Effects 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
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- 208000024891 symptom Diseases 0.000 abstract description 13
- 239000000203 mixture Substances 0.000 description 111
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 101
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 95
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- 239000007858 starting material Substances 0.000 description 64
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 60
- 239000000243 solution Substances 0.000 description 54
- WRYNUJYAXVDTCB-UHFFFAOYSA-M acetyloxymercury Chemical compound CC(=O)O[Hg] WRYNUJYAXVDTCB-UHFFFAOYSA-M 0.000 description 40
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 27
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- 239000011541 reaction mixture Substances 0.000 description 24
- 239000000047 product Substances 0.000 description 23
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 22
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 19
- 239000013078 crystal Substances 0.000 description 19
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 16
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- RQSCFNPNNLWQBJ-UHFFFAOYSA-N 2-methyl-1,3,4-thiadiazole Chemical compound CC1=NN=CS1 RQSCFNPNNLWQBJ-UHFFFAOYSA-N 0.000 description 14
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- 210000004881 tumor cell Anatomy 0.000 description 1
- 210000003708 urethra Anatomy 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 229940102001 zinc bromide Drugs 0.000 description 1
Classifications
-
- 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
- C07D417/02—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 two hetero rings
- C07D417/04—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 two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
- C07D253/08—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 condensed with carbocyclic rings or ring systems
- C07D253/10—Condensed 1,2,4-triazines; Hydrogenated condensed 1,2,4-triazines
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/02—Nasal agents, e.g. decongestants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
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- 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
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
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- 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
- A61P13/10—Drugs for disorders of the urinary system of the bladder
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
-
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P21/02—Muscle relaxants, e.g. for tetanus or cramps
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/04—Drugs for disorders of the muscular or neuromuscular system for myasthenia gravis
-
- 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
-
- 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
- A61P25/08—Antiepileptics; Anticonvulsants
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- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
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- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P27/02—Ophthalmic agents
- A61P27/06—Antiglaucoma agents or miotics
-
- 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
- A61P27/16—Otologicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- 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
- C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
- C07D243/02—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Pulmonology (AREA)
- Physical Education & Sports Medicine (AREA)
- Pain & Pain Management (AREA)
- Diabetes (AREA)
- Urology & Nephrology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Psychology (AREA)
- Ophthalmology & Optometry (AREA)
- Rheumatology (AREA)
- Psychiatry (AREA)
- Immunology (AREA)
- Heart & Thoracic Surgery (AREA)
- Vascular Medicine (AREA)
- Hematology (AREA)
- Hospice & Palliative Care (AREA)
- Obesity (AREA)
- Cardiology (AREA)
- Endocrinology (AREA)
- Emergency Medicine (AREA)
- Otolaryngology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/358,053 US6858605B2 (en) | 2003-02-04 | 2003-02-04 | Substituted 2,3-benzodiazepine derivatives |
| US?10/358,053? | 2003-02-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20050105443A true KR20050105443A (ko) | 2005-11-04 |
Family
ID=32771128
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020057013696A Withdrawn KR20050105443A (ko) | 2003-02-04 | 2004-02-03 | 신규한 치환된 2,3-벤조디아제핀 유도체 |
Country Status (16)
| Country | Link |
|---|---|
| US (2) | US6858605B2 (enExample) |
| EP (1) | EP1592673A4 (enExample) |
| JP (1) | JP2006516647A (enExample) |
| KR (1) | KR20050105443A (enExample) |
| CN (1) | CN1747938A (enExample) |
| AR (1) | AR043023A1 (enExample) |
| AU (1) | AU2004208825A1 (enExample) |
| BR (1) | BRPI0407247A (enExample) |
| CA (1) | CA2512616A1 (enExample) |
| HR (1) | HRP20050765A2 (enExample) |
| MX (1) | MXPA05008236A (enExample) |
| NO (1) | NO20054067L (enExample) |
| RU (1) | RU2005127584A (enExample) |
| TW (1) | TW200500347A (enExample) |
| WO (1) | WO2004069197A2 (enExample) |
| ZA (1) | ZA200505352B (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE602004030663D1 (de) * | 2003-03-05 | 2011-02-03 | Toray Industries | Aromatisches polymer, folie, elektrolytmembran und separator |
| CN101208318B (zh) * | 2003-10-15 | 2010-11-03 | 住友化学株式会社 | 1,2,4-噻二唑化合物和包含其的害虫控制组合物 |
| US20090233913A1 (en) * | 2005-12-30 | 2009-09-17 | Istvan Ling | Optical isomers of dihydro-2,3-benzodiazepines and their stereoselective synthesis |
| RU2314829C1 (ru) * | 2006-03-21 | 2008-01-20 | Войсковая Часть 41598 | Композиция для терапии судорожного синдрома |
| TW200902024A (en) * | 2007-04-02 | 2009-01-16 | Teva Pharma | Novel 2,3-benzodiazepine derivatives and their use as antipsychotic agents |
| EA201590356A1 (ru) * | 2012-08-16 | 2015-07-30 | Байер Фарма Акциенгезельшафт | 2,3-бензодиазепины |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU191698B (en) | 1984-07-27 | 1987-03-30 | Gyogyszerkutato Intezet | Process for producing new 1-aryl-5h-2beta-benzodiazepines |
| HU219778B (hu) | 1990-12-21 | 2001-07-30 | Gyógyszerkutató Intézet Közös Vállalat | Eljárás N-acil-2,3-benzodiazepin-származékok, savaddíciós sóik és az ezeket tartalmazó gyógyászati készítmények előállítására, valamint a vegyületek egy csoportja, és az ezeket tartalmazó gyógyászati készítmények |
| HU206719B (en) | 1990-12-21 | 1992-12-28 | Gyogyszerkutato Intezet | Process for producing 1-/4-acylamino-phenyl/-7,8-methylenedioxy-5h-2,3-benzodiazepine derivatives, acid addicional salts and pharmaceutical compositions containing them |
| HU219777B (hu) | 1993-07-02 | 2001-07-30 | Gyógyszerkutató Intézet Kft. | Optikailag aktív 1-(4-nitro-fenil)-4-metil-7,8-metiléndioxi-3,4-dihidro-5H-2,3-benzodiazepin és eljárás előállítására |
| DE4428835A1 (de) | 1994-08-01 | 1996-02-08 | Schering Ag | Neue 3-substituierte 3H-2,3-Benzodiazepinderivate, deren Herstellung und Verwendung als Arzneimittel |
| PT1157992E (pt) | 1994-08-31 | 2005-10-31 | Lilly Co Eli | Derivados de di-hidro-2,3-benzodiazepina |
| TR199501071A2 (tr) | 1994-08-31 | 1996-06-21 | Lilly Co Eli | Dihidro-2,3-benzodiazepin türevlerinin üretilmesi icin stereoselektif islem. |
| DE19604920A1 (de) | 1996-02-01 | 1997-08-07 | Schering Ag | Neue 2,3-Benzodiazepinderivate, deren Herstellung und Verwendung als Arzneimittel |
| HU9600871D0 (en) | 1996-04-04 | 1996-05-28 | Gyogyszerkutato Intezet | New 2,3-benzodiazepine derivatives |
| UA67749C2 (uk) | 1997-08-12 | 2004-07-15 | Егіш Дьйодьсердьяр Рт. | Похідна 8-заміщеного-9н-1,3-діоксол/4,5-h//2,3/бензодіазепіну з властивостями амра/каїнатного антагоніста, спосіб одержання похідних, фармацевтична композиція (варіанти), спосіб її одержання та спосіб лікування |
| JP2001512731A (ja) | 1997-08-12 | 2001-08-28 | エギシュ ヂョヂセルヂャール エルテー | ＡＭＰＡ／Ｋａｉｎａｔｅ受容体阻害剤としての１，３−ジオキソロ／４，５−Ｈ／２，３／ベンゾジアゼピン誘導体 |
| HU227128B1 (en) | 1999-07-07 | 2010-07-28 | Egyt Gyogyszervegyeszeti Gyar | New 2,3-benzodiazepine derivatives |
-
2003
- 2003-02-04 US US10/358,053 patent/US6858605B2/en not_active Expired - Fee Related
-
2004
- 2004-02-03 HR HR20050765A patent/HRP20050765A2/xx not_active Application Discontinuation
- 2004-02-03 CN CNA200480003526XA patent/CN1747938A/zh active Pending
- 2004-02-03 WO PCT/US2004/003041 patent/WO2004069197A2/en not_active Ceased
- 2004-02-03 CA CA002512616A patent/CA2512616A1/en not_active Abandoned
- 2004-02-03 AU AU2004208825A patent/AU2004208825A1/en not_active Abandoned
- 2004-02-03 JP JP2006503283A patent/JP2006516647A/ja not_active Withdrawn
- 2004-02-03 RU RU2005127584/04A patent/RU2005127584A/ru not_active Application Discontinuation
- 2004-02-03 US US10/771,847 patent/US20070027143A1/en not_active Abandoned
- 2004-02-03 ZA ZA200505352A patent/ZA200505352B/xx unknown
- 2004-02-03 EP EP04707792A patent/EP1592673A4/en not_active Withdrawn
- 2004-02-03 KR KR1020057013696A patent/KR20050105443A/ko not_active Withdrawn
- 2004-02-03 BR BR0407247-2A patent/BRPI0407247A/pt not_active IP Right Cessation
- 2004-02-03 MX MXPA05008236A patent/MXPA05008236A/es not_active Application Discontinuation
- 2004-02-04 TW TW093102551A patent/TW200500347A/zh unknown
- 2004-02-04 AR ARP040100342A patent/AR043023A1/es not_active Application Discontinuation
-
2005
- 2005-09-01 NO NO20054067A patent/NO20054067L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| CN1747938A (zh) | 2006-03-15 |
| EP1592673A2 (en) | 2005-11-09 |
| US20070027143A1 (en) | 2007-02-01 |
| AU2004208825A1 (en) | 2004-08-19 |
| TW200500347A (en) | 2005-01-01 |
| AR043023A1 (es) | 2005-07-13 |
| WO2004069197A2 (en) | 2004-08-19 |
| ZA200505352B (en) | 2007-01-31 |
| EP1592673A4 (en) | 2006-10-25 |
| NO20054067D0 (no) | 2005-09-01 |
| US20040152693A1 (en) | 2004-08-05 |
| BRPI0407247A (pt) | 2006-01-31 |
| MXPA05008236A (es) | 2006-01-17 |
| CA2512616A1 (en) | 2004-08-19 |
| RU2005127584A (ru) | 2006-01-27 |
| HRP20050765A2 (en) | 2006-10-31 |
| NO20054067L (no) | 2005-10-25 |
| JP2006516647A (ja) | 2006-07-06 |
| US6858605B2 (en) | 2005-02-22 |
| WO2004069197A3 (en) | 2005-08-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PA0105 | International application |
Patent event date: 20050725 Patent event code: PA01051R01D Comment text: International Patent Application |
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| PG1501 | Laying open of application | ||
| PC1203 | Withdrawal of no request for examination | ||
| WITN | Application deemed withdrawn, e.g. because no request for examination was filed or no examination fee was paid |