AP551A - 1.5 Benzodiazepine - Google Patents

1.5 Benzodiazepine Download PDF

Info

Publication number: AP551A
Authority: AP; ARIPO
Prior art keywords: phenyl; acetamide; dioxo; diazepin; isopropyl
Prior art date: 1994-04-15

Application number

APAP/P/1995/000731A

Other languages

English (en)

Other versions

AP9500731A0 (en

Inventor

Christopher Joseph Aquino

Markus Brackeen

Milana Dezube

Peter Walter Jeffs

Brad Richard Henke

Edward Martin Suh

Timothy Mark Willson

Gavin Charles Hirst

Tanya Momtahen

Elizabeth Ellen Sugg

Original Assignee

Glaxo Wellcome Inc

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.)

1994-04-15

Filing date

1995-04-13

Publication date

1996-11-01

1994-04-15 Priority claimed from GB9407467A external-priority patent/GB9407467D0/en

1994-10-14 Priority claimed from GB9420700A external-priority patent/GB9420700D0/en

1995-04-13 Application filed by Glaxo Wellcome Inc filed Critical Glaxo Wellcome Inc

1995-04-30 Publication of AP9500731A0 publication Critical patent/AP9500731A0/xx

1996-11-01 Application granted granted Critical

1996-11-01 Publication of AP551A publication Critical patent/AP551A/en

Links

SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 title description 9
229940049706 benzodiazepine Drugs 0.000 title description 6
150000001875 compounds Chemical class 0.000 claims abstract description 229
-1 c3-c6cycloalkyl Chemical group 0.000 claims abstract description 137
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 75
239000001257 hydrogen Substances 0.000 claims abstract description 73
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 72
238000000034 method Methods 0.000 claims abstract description 39
150000002431 hydrogen Chemical group 0.000 claims abstract description 33
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 31
150000002367 halogens Chemical group 0.000 claims abstract description 30
125000001072 heteroaryl group Chemical group 0.000 claims abstract description 29
ZVAPWJGRRUHKGP-UHFFFAOYSA-N 1h-1,5-benzodiazepine Chemical class N1C=CC=NC2=CC=CC=C12 ZVAPWJGRRUHKGP-UHFFFAOYSA-N 0.000 claims abstract description 24
125000005842 heteroatom Chemical group 0.000 claims abstract description 23
229910052736 halogen Inorganic materials 0.000 claims abstract description 22
125000000217 alkyl group Chemical group 0.000 claims abstract description 20
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 20
229920006395 saturated elastomer Polymers 0.000 claims abstract description 19
210000000232 gallbladder Anatomy 0.000 claims abstract description 13
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 10
125000001424 substituent group Chemical group 0.000 claims abstract description 10
LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 claims abstract description 8
230000008569 process Effects 0.000 claims abstract description 7
208000008589 Obesity Diseases 0.000 claims abstract description 5
235000020824 obesity Nutrition 0.000 claims abstract description 5
DQFQCHIDRBIESA-UHFFFAOYSA-N 1-benzazepine Chemical compound N1C=CC=CC2=CC=CC=C12 DQFQCHIDRBIESA-UHFFFAOYSA-N 0.000 claims abstract description 4
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 112
238000006243 chemical reaction Methods 0.000 claims description 72
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 55
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 34
239000002253 acid Substances 0.000 claims description 27
238000002360 preparation method Methods 0.000 claims description 23
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 19
229910052760 oxygen Inorganic materials 0.000 claims description 18
229910052717 sulfur Inorganic materials 0.000 claims description 18
125000003118 aryl group Chemical group 0.000 claims description 17
229910052757 nitrogen Inorganic materials 0.000 claims description 16
125000006239 protecting group Chemical group 0.000 claims description 16
150000003839 salts Chemical class 0.000 claims description 16
210000002784 stomach Anatomy 0.000 claims description 16
239000011737 fluorine Substances 0.000 claims description 14
229910052731 fluorine Inorganic materials 0.000 claims description 14
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
239000008194 pharmaceutical composition Substances 0.000 claims description 14
230000030136 gastric emptying Effects 0.000 claims description 13
125000004076 pyridyl group Chemical group 0.000 claims description 13
125000001041 indolyl group Chemical group 0.000 claims description 12
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 11
230000008602 contraction Effects 0.000 claims description 11
HSUGRBWQSSZJOP-RTWAWAEBSA-N diltiazem Chemical group C1=CC(OC)=CC=C1[C@H]1[C@@H](OC(C)=O)C(=O)N(CCN(C)C)C2=CC=CC=C2S1 HSUGRBWQSSZJOP-RTWAWAEBSA-N 0.000 claims description 11
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
125000001153 fluoro group Chemical group F* 0.000 claims description 10
230000004044 response Effects 0.000 claims description 10
230000028327 secretion Effects 0.000 claims description 10
239000000010 aprotic solvent Substances 0.000 claims description 9
125000005605 benzo group Chemical group 0.000 claims description 9
150000004985 diamines Chemical class 0.000 claims description 9
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 9
125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 9
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 8
150000001412 amines Chemical class 0.000 claims description 8
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 7
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 7
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 7
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
230000000694 effects Effects 0.000 claims description 7
125000000714 pyrimidinyl group Chemical group 0.000 claims description 7
125000001544 thienyl group Chemical group 0.000 claims description 7
241000124008 Mammalia Species 0.000 claims description 6
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 6
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
125000004093 cyano group Chemical group *C#N 0.000 claims description 6
239000003814 drug Substances 0.000 claims description 6
239000008103 glucose Substances 0.000 claims description 6
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 6
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 5
102100021022 Gastrin Human genes 0.000 claims description 5
108010052343 Gastrins Proteins 0.000 claims description 5
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims description 5
239000000969 carrier Substances 0.000 claims description 5
AOXOCDRNSPFDPE-UKEONUMOSA-N chembl413654 Chemical compound C([C@H](C(=O)NCC(=O)N[C@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@H](CCSC)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC=1C=CC=CC=1)C(N)=O)NC(=O)[C@@H](C)NC(=O)[C@@H](CCC(O)=O)NC(=O)[C@@H](CCC(O)=O)NC(=O)[C@@H](CCC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H]1N(CCC1)C(=O)CNC(=O)[C@@H](N)CCC(O)=O)C1=CC=C(O)C=C1 AOXOCDRNSPFDPE-UKEONUMOSA-N 0.000 claims description 5
206010012601 diabetes mellitus Diseases 0.000 claims description 5
201000010099 disease Diseases 0.000 claims description 5
150000004820 halides Chemical class 0.000 claims description 5
230000001939 inductive effect Effects 0.000 claims description 5
239000000546 pharmaceutical excipient Substances 0.000 claims description 5
125000000335 thiazolyl group Chemical group 0.000 claims description 5
208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 5
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 4
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 4
230000037406 food intake Effects 0.000 claims description 4
235000012631 food intake Nutrition 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 4
125000002883 imidazolyl group Chemical group 0.000 claims description 4
NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 claims description 4
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
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125000003226 pyrazolyl group Chemical group 0.000 claims description 4
230000036186 satiety Effects 0.000 claims description 4
235000019627 satiety Nutrition 0.000 claims description 4
229910052727 yttrium Inorganic materials 0.000 claims description 4
208000019901 Anxiety disease Diseases 0.000 claims description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 3
102000004190 Enzymes Human genes 0.000 claims description 3
108090000790 Enzymes Proteins 0.000 claims description 3
229910006069 SO3H Inorganic materials 0.000 claims description 3
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
150000001350 alkyl halides Chemical class 0.000 claims description 3
230000036506 anxiety Effects 0.000 claims description 3
229910052794 bromium Inorganic materials 0.000 claims description 3
125000004181 carboxyalkyl group Chemical group 0.000 claims description 3
210000003169 central nervous system Anatomy 0.000 claims description 3
239000002702 enteric coating Substances 0.000 claims description 3
238000009505 enteric coating Methods 0.000 claims description 3
125000002541 furyl group Chemical group 0.000 claims description 3
230000002496 gastric effect Effects 0.000 claims description 3
125000001786 isothiazolyl group Chemical group 0.000 claims description 3
125000000842 isoxazolyl group Chemical group 0.000 claims description 3
230000002503 metabolic effect Effects 0.000 claims description 3
125000002757 morpholinyl group Chemical group 0.000 claims description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 3
125000002971 oxazolyl group Chemical group 0.000 claims description 3
125000004430 oxygen atom Chemical group O* 0.000 claims description 3
125000003386 piperidinyl group Chemical group 0.000 claims description 3
125000003373 pyrazinyl group Chemical group 0.000 claims description 3
125000002098 pyridazinyl group Chemical group 0.000 claims description 3
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 3
125000000168 pyrrolyl group Chemical group 0.000 claims description 3
125000004434 sulfur atom Chemical group 0.000 claims description 3
125000001113 thiadiazolyl group Chemical group 0.000 claims description 3
125000004568 thiomorpholinyl group Chemical group 0.000 claims description 3
125000006590 (C2-C6) alkenylene group Chemical group 0.000 claims description 2
ARRXCYJTDQGCDO-UHFFFAOYSA-N 2-[2,4-dioxo-5-phenyl-3-(phenylmethoxymethyl)-1,5-benzodiazepin-1-yl]-n-(4-methoxyphenyl)-n-propan-2-ylacetamide Chemical compound C1=CC(OC)=CC=C1N(C(C)C)C(=O)CN1C(=O)C(COCC=2C=CC=CC=2)C(=O)N(C=2C=CC=CC=2)C2=CC=CC=C21 ARRXCYJTDQGCDO-UHFFFAOYSA-N 0.000 claims description 2
VOUAQYXWVJDEQY-QENPJCQMSA-N 33017-11-7 Chemical compound OC(=O)CC[C@H](N)C(=O)N[C@@H](C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](C(C)C)C(=O)NCC(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)NCC(=O)NCC(=O)N1CCC[C@H]1C(=O)NCC(=O)N[C@@H](C)C(=O)NCC(=O)N[C@@H](CO)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(N)=O)C(=O)N1[C@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)NCC(=O)N[C@@H](CO)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(N)=O)C(O)=O)CCC1 VOUAQYXWVJDEQY-QENPJCQMSA-N 0.000 claims description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
108010075254 C-Peptide Proteins 0.000 claims description 2
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102000004877 Insulin Human genes 0.000 claims description 2
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206010022489 Insulin Resistance Diseases 0.000 claims description 2
125000004103 aminoalkyl group Chemical group 0.000 claims description 2
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims description 2
239000008280 blood Substances 0.000 claims description 2
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125000002576 diazepinyl group Chemical group N1N=C(C=CC=C1)* 0.000 claims description 2
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229910052740 iodine Inorganic materials 0.000 claims description 2
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238000007410 oral glucose tolerance test Methods 0.000 claims description 2
238000005932 reductive alkylation reaction Methods 0.000 claims description 2
238000002560 therapeutic procedure Methods 0.000 claims description 2
BWPIHGUNTHDNTK-UHFFFAOYSA-N 2-[3-(2h-indazol-3-ylmethyl)-2,4-dioxo-5-pyridin-3-yl-1,5-benzodiazepin-1-yl]-n-(4-methoxyphenyl)-n-propan-2-ylacetamide Chemical compound C1=CC(OC)=CC=C1N(C(C)C)C(=O)CN1C(=O)C(CC=2C3=CC=CC=C3NN=2)C(=O)N(C=2C=NC=CC=2)C2=CC=CC=C21 BWPIHGUNTHDNTK-UHFFFAOYSA-N 0.000 claims 2
230000001225 therapeutic effect Effects 0.000 claims 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
LXAVCNBKXZQWGB-UHFFFAOYSA-N 2-[3-(1-benzothiophen-3-ylmethyl)-2,4-dioxo-5-phenyl-1,5-benzodiazepin-1-yl]-n-(4-methoxyphenyl)-n-propan-2-ylacetamide Chemical compound C1=CC(OC)=CC=C1N(C(C)C)C(=O)CN1C(=O)C(CC=2C3=CC=CC=C3SC=2)C(=O)N(C=2C=CC=CC=2)C2=CC=CC=C21 LXAVCNBKXZQWGB-UHFFFAOYSA-N 0.000 claims 1
ONCTXYTWLYUWTC-UHFFFAOYSA-N 2-[3-[(6-fluoro-2h-indazol-3-yl)methyl]-2,4-dioxo-5-phenyl-1,5-benzodiazepin-1-yl]-n-phenyl-n-propan-2-ylacetamide Chemical compound C=1C=CC=CC=1N(C(C)C)C(=O)CN(C(C(CC=1C2=CC=C(F)C=C2NN=1)C1=O)=O)C2=CC=CC=C2N1C1=CC=CC=C1 ONCTXYTWLYUWTC-UHFFFAOYSA-N 0.000 claims 1
QOONXFHKOGXASQ-UHFFFAOYSA-N 2-[3-[(6-fluoro-2h-indazol-3-yl)methyl]-2,4-dioxo-5-phenyl-1,5-benzodiazepin-1-yl]-n-propan-2-yl-n-[4-(trifluoromethoxy)phenyl]acetamide Chemical compound C=1C=C(OC(F)(F)F)C=CC=1N(C(C)C)C(=O)CN(C(C(CC=1C2=CC=C(F)C=C2NN=1)C1=O)=O)C2=CC=CC=C2N1C1=CC=CC=C1 QOONXFHKOGXASQ-UHFFFAOYSA-N 0.000 claims 1
GJGGQFHEPYGYPC-UHFFFAOYSA-N 2-[3-methyl-2,4-dioxo-1-[2-oxo-2-(n-propan-2-ylanilino)ethyl]-5-phenyl-1,5-benzodiazepin-3-yl]-n-phenylacetamide Chemical compound C=1C=CC=CC=1N(C(C)C)C(=O)CN(C(C(C)(CC(=O)NC=1C=CC=CC=1)C1=O)=O)C2=CC=CC=C2N1C1=CC=CC=C1 GJGGQFHEPYGYPC-UHFFFAOYSA-N 0.000 claims 1
OTJMDLIUFVHKNU-UHFFFAOYSA-N 2-hydroxy-5-methylidene-3-(piperidin-1-ylamino)cyclopent-2-en-1-one Chemical compound C1C(=C)C(=O)C(O)=C1NN1CCCCC1 OTJMDLIUFVHKNU-UHFFFAOYSA-N 0.000 claims 1
101001030284 Homo sapiens Methylthioribulose-1-phosphate dehydratase Proteins 0.000 claims 1
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SNIOPGDIGTZGOP-UHFFFAOYSA-N Nitroglycerin Chemical compound [O-][N+](=O)OCC(O[N+]([O-])=O)CO[N+]([O-])=O SNIOPGDIGTZGOP-UHFFFAOYSA-N 0.000 claims 1
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XVAIDCNLVLTVFM-UHFFFAOYSA-N methacetin Chemical compound COC1=CC=C(NC(C)=O)C=C1 XVAIDCNLVLTVFM-UHFFFAOYSA-N 0.000 claims 1
LOXHZBJMXMSEOS-UHFFFAOYSA-N n-(4-fluorophenyl)-2-[3-(2h-indazol-3-ylmethyl)-2,4-dioxo-5-phenyl-1,5-benzodiazepin-1-yl]-n-propan-2-ylacetamide Chemical compound C=1C=C(F)C=CC=1N(C(C)C)C(=O)CN(C(C(CC=1C2=CC=CC=C2NN=1)C1=O)=O)C2=CC=CC=C2N1C1=CC=CC=C1 LOXHZBJMXMSEOS-UHFFFAOYSA-N 0.000 claims 1
NDMKAESGNQHGID-UHFFFAOYSA-N n-(4-methoxyphenyl)-2-[3-methyl-3-[(1-methylindol-3-yl)methyl]-2,4-dioxo-5-phenyl-1,5-benzodiazepin-1-yl]-n-propan-2-ylacetamide Chemical compound C1=CC(OC)=CC=C1N(C(C)C)C(=O)CN1C(=O)C(C)(CC=2C3=CC=CC=C3N(C)C=2)C(=O)N(C=2C=CC=CC=2)C2=CC=CC=C21 NDMKAESGNQHGID-UHFFFAOYSA-N 0.000 claims 1
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125000004429 atom Chemical group 0.000 abstract 1
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WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 167
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230000000699 topical effect Effects 0.000 description 1
125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
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LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-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
- C07D401/04—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 directly linked by a ring-member-to-ring-member bond
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
- C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
- C07D243/10—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D243/12—1,5-Benzodiazepines; Hydrogenated 1,5-benzodiazepines
- 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
- C07D401/14—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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- 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
- C07D405/06—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 carbon chain containing only aliphatic carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
- 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
- C07D413/06—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 carbon chain containing only aliphatic carbon atoms
- 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

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Life Sciences & Earth Sciences (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Engineering & Computer Science (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Diabetes (AREA)
Obesity (AREA)
Hematology (AREA)
Child & Adolescent Psychology (AREA)
Gastroenterology & Hepatology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

APAP/P/1995/000731A 1994-04-15 1995-04-13 1.5 Benzodiazepine AP551A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB9407467A GB9407467D0 (en)	1994-04-15	1994-04-15	1,5 Benzodiazepine compounds
GB9420700A GB9420700D0 (en)	1994-10-14	1994-10-14	Heterocyclic compounds

Publications (2)

Publication Number	Publication Date
AP9500731A0 AP9500731A0 (en)	1995-04-30
AP551A true AP551A (en)	1996-11-01

Family

ID=26304709

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
APAP/P/1995/000731A AP551A (en)	1994-04-15	1995-04-13	1.5 Benzodiazepine

Country Status (12)

Country	Link
US (1)	US5859007A (fr)
EP (1)	EP0755384A1 (fr)
JP (1)	JPH09511999A (fr)
AP (1)	AP551A (fr)
AU (1)	AU2306295A (fr)
CA (1)	CA2186872A1 (fr)
IL (1)	IL113366A0 (fr)
MA (1)	MA23504A1 (fr)
MX (1)	MX9604770A (fr)
PE (1)	PE27497A1 (fr)
TN (1)	TNSN95039A1 (fr)
WO (1)	WO1995028391A1 (fr)

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5739129A (en) *	1994-04-14	1998-04-14	Glaxo Wellcome Inc.	CCK or gastrin modulating 5-heterocyclic-1, 5 benzodiazepines
US6768024B1 (en)	2000-08-04	2004-07-27	Lion Bioscience Ag	Triamine derivative melanocortin receptor ligands and methods of using same
AP2006003768A0 (en) *	2004-05-25	2006-10-31	Pfizer Prod Inc	TetraazabenzoÄeÜazulene derivatives and analogs tehereof
KR100840852B1 (ko) *	2004-05-25	2008-06-23	화이자 프로덕츠 인크.	테트라아자벤조[ｅ]아줄렌 유도체 및 이의 유사체
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Also Published As

Publication number	Publication date
TNSN95039A1 (fr)	1996-02-06
AU2306295A (en)	1995-11-10
IL113366A0 (en)	1995-07-31
AP9500731A0 (en)	1995-04-30
MX9604770A (es)	1998-05-31
US5859007A (en)	1999-01-12
CA2186872A1 (fr)	1995-10-26
PE27497A1 (es)	1997-08-07
EP0755384A1 (fr)	1997-01-29
JPH09511999A (ja)	1997-12-02
MA23504A1 (fr)	1995-12-31
WO1995028391A1 (fr)	1995-10-26

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CN110621664B (zh)	2023-08-01	新型哌啶-2,6-二酮衍生物及其用途
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CZ269698A3 (cs)	1999-10-13	Inhibitory farnesyl protein transferázy
JPH10511929A (ja)	1998-11-17	Ｃｃｋ−ａレセプターに対してアゴニスト活性を有するアシルアミノアセタミド誘導体
KR20020067938A (ko)	2002-08-24	신규한 1,3-디히드로-2ｈ-인돌-2-온 유도체들, 이들을제조하는 방법, 및 이들을 포함하는 제약 조성물
HUT71339A (en)	1995-11-28	1,4-benzodiazepine derivatives and pharmaceutical compositions containing them
WO2005019188A1 (fr)	2005-03-03	Derive de pyrimidine fusionne et utilisation associee
RU2152939C1 (ru)	2000-07-20	5-гетероцикло-1,5-бензодиазепины и их фармацевтически приемлемые соли
JP2008516975A (ja)	2008-05-22	化合物
KR100750028B1 (ko)	2007-08-16	치료에 유용한 트리아졸 화합물
WO2001040197A1 (fr)	2001-06-07	Sels de calcium de derives de 1,5-benzodiazepine, procede de fabrication de ces sels et medicaments les renfermant