SK19142001A3 - Derivát dihydrobenzodiazepínu, spôsob jeho prípravy a jeho použitie na liečenie dislipidémie - Google Patents

Derivát dihydrobenzodiazepínu, spôsob jeho prípravy a jeho použitie na liečenie dislipidémie Download PDF

Info

Publication number: SK19142001A3
Authority: SK; Slovakia
Prior art keywords: alkyl; group; aryl; optionally substituted; optionally
Prior art date: 1999-07-06

Application number

SK1914-2001A

Other languages

English (en)

Slovak (sk)

Inventor

Jean-Jacques Berthelon

Daniel Guerrier

Michel Brunet

Jean-Jacques Zeiller

Francis Contard

Frederic Ausseil

Original Assignee

Merck Patent Gmbh

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.)

1999-07-06

Filing date

2000-07-04

Publication date

2002-06-04

2000-07-04 Application filed by Merck Patent Gmbh filed Critical Merck Patent Gmbh

2002-06-04 Publication of SK19142001A3 publication Critical patent/SK19142001A3/sk

Links

208000032928 Dyslipidaemia Diseases 0.000 title claims abstract description 8
208000017170 Lipid metabolism disease Diseases 0.000 title claims abstract description 8
201000001320 Atherosclerosis Diseases 0.000 claims abstract description 10
206010012601 diabetes mellitus Diseases 0.000 claims abstract description 7
SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical class N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 claims abstract 3
150000001875 compounds Chemical class 0.000 claims description 128
125000003118 aryl group Chemical group 0.000 claims description 127
125000004432 carbon atom Chemical group C* 0.000 claims description 75
125000000217 alkyl group Chemical group 0.000 claims description 72
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 60
125000001424 substituent group Chemical group 0.000 claims description 51
125000001072 heteroaryl group Chemical group 0.000 claims description 50
229910052739 hydrogen Inorganic materials 0.000 claims description 42
239000001257 hydrogen Substances 0.000 claims description 41
-1 nitro, hydroxyl Chemical group 0.000 claims description 41
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 40
125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 39
238000002360 preparation method Methods 0.000 claims description 39
229910052736 halogen Inorganic materials 0.000 claims description 37
125000000623 heterocyclic group Chemical group 0.000 claims description 37
125000005843 halogen group Chemical group 0.000 claims description 35
150000002367 halogens Chemical class 0.000 claims description 35
UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical group [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 35
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 34
238000006243 chemical reaction Methods 0.000 claims description 33
229910052717 sulfur Inorganic materials 0.000 claims description 32
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 31
125000003545 alkoxy group Chemical group 0.000 claims description 28
238000000034 method Methods 0.000 claims description 28
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 27
229910052757 nitrogen Inorganic materials 0.000 claims description 27
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 23
239000002253 acid Substances 0.000 claims description 21
125000006702 (C1-C18) alkyl group Chemical group 0.000 claims description 19
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 18
125000002947 alkylene group Chemical group 0.000 claims description 18
229910052760 oxygen Inorganic materials 0.000 claims description 18
239000011593 sulfur Chemical group 0.000 claims description 18
125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 16
125000000041 C6-C10 aryl group Chemical group 0.000 claims description 15
239000001301 oxygen Substances 0.000 claims description 15
125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 claims description 14
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 14
125000005842 heteroatom Chemical group 0.000 claims description 14
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 13
150000003839 salts Chemical class 0.000 claims description 13
125000000753 cycloalkyl group Chemical group 0.000 claims description 12
230000008569 process Effects 0.000 claims description 12
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 11
150000001557 benzodiazepines Chemical class 0.000 claims description 11
125000004043 oxo group Chemical group O=* 0.000 claims description 11
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 10
229910052799 carbon Inorganic materials 0.000 claims description 10
125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 9
UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
125000004433 nitrogen atom Chemical group N* 0.000 claims description 9
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical class CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 8
125000003710 aryl alkyl group Chemical group 0.000 claims description 8
125000005129 aryl carbonyl group Chemical group 0.000 claims description 7
125000004104 aryloxy group Chemical group 0.000 claims description 7
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 7
150000007513 acids Chemical class 0.000 claims description 6
125000003342 alkenyl group Chemical group 0.000 claims description 6
125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 6
125000004391 aryl sulfonyl group Chemical group 0.000 claims description 6
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
125000004093 cyano group Chemical group *C#N 0.000 claims description 6
125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 5
125000006239 protecting group Chemical group 0.000 claims description 5
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 4
150000007933 aliphatic carboxylic acids Chemical class 0.000 claims description 4
125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 4
125000004414 alkyl thio group Chemical group 0.000 claims description 4
125000005530 alkylenedioxy group Chemical group 0.000 claims description 4
125000005110 aryl thio group Chemical group 0.000 claims description 4
125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
125000004434 sulfur atom Chemical group 0.000 claims description 4
QABXUUGOQUQSOK-UHFFFAOYSA-N 4-(5,6-dihydro-[1,3]thiazolo[2,3-b][1,3]benzodiazepin-3-yl)benzene-1,2-diol Chemical compound C1=C(O)C(O)=CC=C1C1=CSC2=NC3=CC=CC=C3CCN12 QABXUUGOQUQSOK-UHFFFAOYSA-N 0.000 claims description 3
239000003814 drug Substances 0.000 claims description 3
125000005553 heteroaryloxy group Chemical group 0.000 claims description 3
150000002500 ions Chemical class 0.000 claims description 3
150000002576 ketones Chemical class 0.000 claims description 3
JNURZOSOBKMRQQ-UHFFFAOYSA-N n-(4,5-dihydro-1h-1,3-benzodiazepin-2-yl)-2-(3,4-dihydroxyphenyl)-2-oxoethanesulfonamide Chemical compound C1=C(O)C(O)=CC=C1C(=O)CS(=O)(=O)NC1=NC2=CC=CC=C2CCN1 JNURZOSOBKMRQQ-UHFFFAOYSA-N 0.000 claims description 3
KIVVIUDQPUWFIA-UHFFFAOYSA-N 7-chloro-3-(4-phenylphenyl)-5,6-dihydro-[1,3]thiazolo[2,3-b][1,3]benzodiazepine Chemical compound N12CCC=3C(Cl)=CC=CC=3N=C2SC=C1C(C=C1)=CC=C1C1=CC=CC=C1 KIVVIUDQPUWFIA-UHFFFAOYSA-N 0.000 claims description 2
GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 2
125000003302 alkenyloxy group Chemical group 0.000 claims description 2
125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 2
125000003282 alkyl amino group Chemical group 0.000 claims description 2
125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 2
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 2
239000002168 alkylating agent Substances 0.000 claims description 2
229940100198 alkylating agent Drugs 0.000 claims description 2
150000001735 carboxylic acids Chemical class 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims description 2
125000000842 isoxazolyl group Chemical group 0.000 claims description 2
239000008194 pharmaceutical composition Substances 0.000 claims description 2
230000002265 prevention Effects 0.000 claims description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 10
125000006719 (C6-C10) aryl (C1-C6) alkyl group Chemical group 0.000 claims 6
125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 3
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims 2
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims 2
229940049706 benzodiazepine Drugs 0.000 claims 2
125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 1
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
125000006374 C2-C10 alkenyl group Chemical group 0.000 claims 1
125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 1
125000000172 C5-C10 aryl group Chemical group 0.000 claims 1
101000649938 Mus musculus Vacuolar protein sorting-associated protein 28 homolog Proteins 0.000 claims 1
150000005840 aryl radicals Chemical class 0.000 claims 1
125000006268 biphenyl-3-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C(*)=C([H])C([H])=C1[H] 0.000 claims 1
239000003153 chemical reaction reagent Substances 0.000 claims 1
125000005283 haloketone group Chemical group 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 36
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 36
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 33
239000002904 solvent Substances 0.000 description 28
239000000243 solution Substances 0.000 description 23
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
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238000010992 reflux Methods 0.000 description 13
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150000001413 amino acids Chemical class 0.000 description 1
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239000012736 aqueous medium Substances 0.000 description 1
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238000004166 bioassay Methods 0.000 description 1
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238000009835 boiling Methods 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
239000000872 buffer Substances 0.000 description 1
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239000003054 catalyst Substances 0.000 description 1
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WCZVZNOTHYJIEI-UHFFFAOYSA-N cinnoline Chemical compound N1=NC=CC2=CC=CC=C21 WCZVZNOTHYJIEI-UHFFFAOYSA-N 0.000 description 1
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238000002425 crystallisation Methods 0.000 description 1
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125000002993 cycloalkylene group Chemical group 0.000 description 1
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239000006185 dispersion Substances 0.000 description 1
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238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
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230000003287 optical effect Effects 0.000 description 1
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125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 1
NQPDZGIKBAWPEJ-UHFFFAOYSA-N pentanoic acid group Chemical class C(CCCC)(=O)O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
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230000003389 potentiating effect Effects 0.000 description 1
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125000001422 pyrrolinyl group Chemical group 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
208000037803 restenosis Diseases 0.000 description 1
229930195734 saturated hydrocarbon Natural products 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
238000000926 separation method Methods 0.000 description 1
210000002966 serum Anatomy 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
238000010186 staining Methods 0.000 description 1
125000003107 substituted aryl group Chemical group 0.000 description 1
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125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 1
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230000001225 therapeutic effect Effects 0.000 description 1
125000001113 thiadiazolyl group Chemical group 0.000 description 1
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230000001988 toxicity Effects 0.000 description 1
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150000003624 transition metals Chemical class 0.000 description 1
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IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
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208000019553 vascular disease Diseases 0.000 description 1
PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- 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
- A61P3/06—Antihyperlipidemics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- 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
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- 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
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
- C07D213/46—Oxygen atoms
- C07D213/50—Ketonic radicals
- 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
- C07D243/04—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 3
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/08—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/40—Radicals substituted by oxygen atoms
- C07D307/46—Doubly bound oxygen atoms, or two oxygen atoms singly bound to the same carbon atom
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D307/80—Radicals substituted by oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
- C07D311/08—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring
- C07D311/16—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring substituted in position 7
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
- 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
- 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
- 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
- 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
- C07D513/12—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 three hetero rings
- C07D513/14—Ortho-condensed systems

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Diabetes (AREA)
General Health & Medical Sciences (AREA)
Hematology (AREA)
Obesity (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Urology & Nephrology (AREA)
Vascular Medicine (AREA)
Emergency Medicine (AREA)
Endocrinology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

SK1914-2001A 1999-07-06 2000-07-04 Derivát dihydrobenzodiazepínu, spôsob jeho prípravy a jeho použitie na liečenie dislipidémie SK19142001A3 (sk)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR9908714A FR2796070B1 (fr)	1999-07-06	1999-07-06	Derives de benzodiazepines utilisables dans le traitement de dyslipidemies, de l'atherosclerose et du diabete, compositions pharmaceutiques les contenant et procedes de preparation
PCT/EP2000/006230 WO2001002373A1 (fr)	1999-07-06	2000-07-04	Dihydrobenzodiazepines et leur utilisation dans le traitement de dyslipidemies

Publications (1)

Publication Number	Publication Date
SK19142001A3 true SK19142001A3 (sk)	2002-06-04

Family

ID=9547763

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK1914-2001A SK19142001A3 (sk)	1999-07-06	2000-07-04	Derivát dihydrobenzodiazepínu, spôsob jeho prípravy a jeho použitie na liečenie dislipidémie

Country Status (22)

Country	Link
US (1)	US7323458B1 (de)
EP (1)	EP1189890B1 (de)
JP (1)	JP4699663B2 (de)
KR (1)	KR20020022763A (de)
CN (1)	CN1359377A (de)
AR (1)	AR031071A1 (de)
AT (1)	ATE323685T1 (de)
AU (1)	AU767016B2 (de)
BR (1)	BR0012169A (de)
CA (1)	CA2378165C (de)
CZ (1)	CZ20014604A3 (de)
DE (1)	DE60027429T2 (de)
ES (1)	ES2258975T3 (de)
FR (1)	FR2796070B1 (de)
HU (1)	HUP0201785A3 (de)
MX (1)	MXPA01013457A (de)
NO (1)	NO20020031L (de)
PL (1)	PL352333A1 (de)
RU (1)	RU2247115C2 (de)
SK (1)	SK19142001A3 (de)
WO (1)	WO2001002373A1 (de)
ZA (1)	ZA200201008B (de)

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DE10142660A1 (de)	2001-08-31	2003-03-20	Aventis Pharma Gmbh	Verwendung von Derivaten von C2-substituierten Indan-1-ol-Systemen zur Herstellung von Medikamenten zur Prophylaxe oder Behandlung von Obesitas
US6677303B2 (en)	2001-04-30	2004-01-13	Syn X Pharma	Biopolymer marker indicative of disease state having a molecular weight of 1097 daltons
US6916850B2 (en) *	2001-05-03	2005-07-12	Galileo Pharmaceuticals, Inc.	Pyruvate derivatives
DE10142722A1 (de) *	2001-08-31	2003-03-27	Aventis Pharma Deutschland GmbH, 65929 Frankfurt	C2-substituierte Indan-1-one und ihre Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel
DE10142659A1 (de)	2001-08-31	2003-03-20	Aventis Pharma Gmbh	Verwendung von mehrfach substituierten Indan-1-ol. Systemen zur Herstellung von Medikamenten zur Prophylaxe oder Behandlung von Obesitas
DE10142668A1 (de)	2001-08-31	2003-03-20	Aventis Pharma Gmbh	Verwendung von C2-substituierten Indan-1-on-Systemen zur Herstellung von Medikamenten zur Prophylaxe oder Behandlung von Obesitas
DE10320732A1 (de) *	2003-05-05	2004-12-09	Friedrich-Schiller-Universität Jena Büro für Forschungstransfer	Neue schnell wirkende Anästhetika und Verfahren zu ihrer Herstellung
CN1819996B (zh) *	2003-07-10	2010-10-27	Osi制药公司	作为细胞色素p450抑制剂的亚萘基衍生物
WO2005009387A2 (en) *	2003-07-23	2005-02-03	X-Ceptor Therapeutics Inc.	Azepine derivatives as pharmaceutical agents
US7598412B2 (en) *	2003-10-08	2009-10-06	Vertex Pharmaceuticals Incorporated	Modulators of ATP-binding cassette transporters
US7662844B2 (en)	2004-07-12	2010-02-16	Osi Pharmaceuticals, Inc.	Naphthylene derivatives as cytochrome P450 inhibitors
WO2006063294A2 (en) *	2004-12-09	2006-06-15	Kalypsys, Inc.	Novel inhibitors of histone deacetylase for the treatment of disease
GB0506133D0 (en) *	2005-03-24	2005-05-04	Sterix Ltd	Compound
KR102585191B1 (ko) *	2020-08-25	2023-10-04	경기대학교 산학협력단	신규한 벤조디아제핀-3-온 유도체 및 이를 포함하는 당뇨병성 신경병증 치료 또는 예방용 약학적 조성물
CN121971448A (zh) *	2026-01-23	2026-05-05	北京大学	一种苯并氮杂䓬衍生物在预防或治疗动脉粥样硬化中的应用

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US3780023A (en) *	1972-06-30	1973-12-18	J Suh	2-aralkylamino-4,5-dihydro-3h-1,3-benzodiazepines
ES484553A1 (es)	1978-10-05	1980-05-16	Hoechst Ag	Un metodo para preparar 4-fenil-1,3-benzodiazepinas
US5260339A (en)	1978-10-05	1993-11-09	Hoechst-Roussel Pharmaceuticals Incorporated	4-phenyl-1,3-benzodiazepines and 2-amino-α-phenylphenethylamines for treating convulsions and protecting neurons
FR2540871B1 (fr) *	1983-02-16	1986-01-10	Lipha	Amino-2 phenyl-5 benzodiazepines-1,3; procede de preparation et medicaments les contenant
FR2550199B1 (fr) *	1983-08-02	1985-11-29	Lipha	Imidazo et pyrimido (2,1-b) benzodiazepines-1,3, procedes de preparation et medicament les contenant
TW245719B (de) *	1990-09-10	1995-04-21	Sterling Winthrop Inc
ZA956647B (en) *	1994-08-10	1997-02-10	Wellcome Found	Hypolipidaemic compounds.
JPH08157369A (ja) *	1994-10-07	1996-06-18	Takeda Chem Ind Ltd	トリグリセライド低下剤
JPH0987260A (ja) *	1995-09-27	1997-03-31	Takeda Chem Ind Ltd	縮合環化合物とその用途

1999
- 1999-07-06 FR FR9908714A patent/FR2796070B1/fr not_active Expired - Fee Related
2000
- 2000-07-04 CA CA2378165A patent/CA2378165C/en not_active Expired - Fee Related
- 2000-07-04 AT AT00945864T patent/ATE323685T1/de not_active IP Right Cessation
- 2000-07-04 RU RU2002102248/04A patent/RU2247115C2/ru not_active IP Right Cessation
- 2000-07-04 DE DE60027429T patent/DE60027429T2/de not_active Expired - Lifetime
- 2000-07-04 CZ CZ20014604A patent/CZ20014604A3/cs unknown
- 2000-07-04 CN CN00809680A patent/CN1359377A/zh active Pending
- 2000-07-04 ES ES00945864T patent/ES2258975T3/es not_active Expired - Lifetime
- 2000-07-04 KR KR1020027000137A patent/KR20020022763A/ko not_active Ceased
- 2000-07-04 SK SK1914-2001A patent/SK19142001A3/sk unknown
- 2000-07-04 AU AU59814/00A patent/AU767016B2/en not_active Ceased
- 2000-07-04 MX MXPA01013457A patent/MXPA01013457A/es unknown
- 2000-07-04 PL PL00352333A patent/PL352333A1/xx unknown
- 2000-07-04 JP JP2001507812A patent/JP4699663B2/ja not_active Expired - Fee Related
- 2000-07-04 WO PCT/EP2000/006230 patent/WO2001002373A1/fr not_active Ceased
- 2000-07-04 EP EP00945864A patent/EP1189890B1/de not_active Expired - Lifetime
- 2000-07-04 US US10/019,683 patent/US7323458B1/en not_active Expired - Fee Related
- 2000-07-04 BR BR0012169-0A patent/BR0012169A/pt not_active IP Right Cessation
- 2000-07-04 HU HU0201785A patent/HUP0201785A3/hu unknown
- 2000-07-06 AR ARP000103436A patent/AR031071A1/es unknown
2002
- 2002-01-04 NO NO20020031A patent/NO20020031L/no not_active Application Discontinuation
- 2002-02-05 ZA ZA200201008A patent/ZA200201008B/en unknown

Also Published As

Publication number	Publication date
DE60027429D1 (de)	2006-05-24
PL352333A1 (en)	2003-08-11
EP1189890B1 (de)	2006-04-19
FR2796070A1 (fr)	2001-01-12
EP1189890A1 (de)	2002-03-27
AR031071A1 (es)	2003-09-10
CZ20014604A3 (cs)	2002-08-14
AU5981400A (en)	2001-01-22
US7323458B1 (en)	2008-01-29
BR0012169A (pt)	2002-03-19
WO2001002373A1 (fr)	2001-01-11
DE60027429T2 (de)	2006-12-14
HUP0201785A2 (hu)	2002-12-28
JP2003503483A (ja)	2003-01-28
FR2796070B1 (fr)	2003-02-21
WO2001002373A8 (fr)	2001-06-14
MXPA01013457A (es)	2002-07-22
ZA200201008B (en)	2003-08-27
CN1359377A (zh)	2002-07-17
ES2258975T3 (es)	2006-09-16
CA2378165A1 (en)	2001-01-11
JP4699663B2 (ja)	2011-06-15
AU767016B2 (en)	2003-10-30
NO20020031D0 (no)	2002-01-04
HUP0201785A3 (en)	2003-02-28
KR20020022763A (ko)	2002-03-27
RU2247115C2 (ru)	2005-02-27
NO20020031L (no)	2002-03-05
ATE323685T1 (de)	2006-05-15
CA2378165C (en)	2010-08-17

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EP2173734B1 (de)	2016-03-23	Chemische verbindungen
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RU2247115C2 (ru)	2005-02-27	Дигидробензодиазепины, способы их получения и фармацевтическая композиция на их основе
TW201028408A (en)	2010-08-01	Compounds
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BRPI0720525A2 (pt)	2014-01-07	Inibidores de quinase mapk/erk
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WO2002055077A1 (en)	2002-07-18	Use of imidazolyl cyclic acetal derivatives in the manufacture of a medicament for the treatment of diseases mediated by the alk5 receptors
EP0905136A1 (de)	1999-03-31	Tetrahydro gamma-Carboline
US9120764B2 (en)	2015-09-01	Chromene derivatives
EP4298102A1 (de)	2024-01-03	Furoindazolderivate als gpr84-antagonisten
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JP4042566B2 (ja)	2008-02-06	ピペリジン化合物およびその医薬用途
Wang et al.	2011	Synthesis and structure–activity relationship of N-(2-arylethyl) isoquinoline derivatives as human scavenger receptor CD36 antagonists
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