NO970684L - Nye N-substituerte naftokondenserte laktamer - Google Patents
Nye N-substituerte naftokondenserte laktamerInfo
- Publication number
- NO970684L NO970684L NO970684A NO970684A NO970684L NO 970684 L NO970684 L NO 970684L NO 970684 A NO970684 A NO 970684A NO 970684 A NO970684 A NO 970684A NO 970684 L NO970684 L NO 970684L
- Authority
- NO
- Norway
- Prior art keywords
- alkyl
- hydrogen
- naphtho
- oxo
- tetrahydro
- Prior art date
Links
- 150000003951 lactams Chemical class 0.000 title description 7
- 150000001875 compounds Chemical class 0.000 claims description 58
- 239000000122 growth hormone Substances 0.000 claims description 39
- 102000018997 Growth Hormone Human genes 0.000 claims description 37
- 108010051696 Growth Hormone Proteins 0.000 claims description 37
- 229910052739 hydrogen Inorganic materials 0.000 claims description 24
- 239000001257 hydrogen Substances 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 24
- 239000000203 mixture Substances 0.000 claims description 22
- -1 3-amino-3-methyl-N-(4-oxo-5-(4-(4-(5-methyl-[1,3,4]oxadiazol-2-yl)-thien-3-yl)benzyl) -2,3,4,5-tetrahydro-1H-naphtho-[2,1-b]azepin-3-yl)butyramide Chemical compound 0.000 claims description 21
- 150000003839 salts Chemical class 0.000 claims description 15
- 229910052736 halogen Inorganic materials 0.000 claims description 13
- 150000002367 halogens Chemical class 0.000 claims description 13
- 206010062767 Hypophysitis Diseases 0.000 claims description 12
- 210000003635 pituitary gland Anatomy 0.000 claims description 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 claims description 7
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 6
- 208000035475 disorder Diseases 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 5
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 230000004936 stimulating effect Effects 0.000 claims description 4
- 125000006564 (C4-C8) cycloalkyl group Chemical group 0.000 claims description 3
- 230000037396 body weight Effects 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 239000002552 dosage form Substances 0.000 claims description 3
- 150000003536 tetrazoles Chemical class 0.000 claims description 3
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims description 3
- 150000003852 triazoles Chemical class 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- PAJPWUMXBYXFCZ-UHFFFAOYSA-N 1-aminocyclopropanecarboxylic acid Chemical compound OC(=O)C1(N)CC1 PAJPWUMXBYXFCZ-UHFFFAOYSA-N 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 238000007911 parenteral administration Methods 0.000 claims description 2
- 230000008569 process Effects 0.000 claims description 2
- 230000002685 pulmonary effect Effects 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000003831 tetrazolyl group Chemical group 0.000 claims 2
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 1
- FKASFBLJDCHBNZ-UHFFFAOYSA-N 1,3,4-oxadiazole Chemical group C1=NN=CO1 FKASFBLJDCHBNZ-UHFFFAOYSA-N 0.000 claims 1
- NNZKRDMTHUGYPF-UHFFFAOYSA-N 3-amino-3-methyl-n-[4-oxo-5-[[4-[2-(2h-tetrazol-5-yl)phenyl]phenyl]methyl]-2,3-dihydro-1h-benzo[g][1]benzazepin-3-yl]butanamide Chemical compound O=C1C(NC(=O)CC(C)(N)C)CCC(C2=CC=CC=C2C=C2)=C2N1CC(C=C1)=CC=C1C1=CC=CC=C1C1=NN=NN1 NNZKRDMTHUGYPF-UHFFFAOYSA-N 0.000 claims 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 238000001802 infusion Methods 0.000 claims 1
- 238000002347 injection Methods 0.000 claims 1
- 239000007924 injection Substances 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 51
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 33
- 239000000243 solution Substances 0.000 description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 25
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 19
- 239000007787 solid Substances 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 239000011541 reaction mixture Substances 0.000 description 18
- 239000002904 solvent Substances 0.000 description 17
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 14
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- 238000001914 filtration Methods 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 11
- 239000000725 suspension Substances 0.000 description 11
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 11
- 239000003480 eluent Substances 0.000 description 10
- 239000012299 nitrogen atmosphere Substances 0.000 description 10
- JUNTXRSHMXBNOU-UHFFFAOYSA-N 3-amino-1,2,3,5-tetrahydrobenzo[g][1]benzazepin-4-one Chemical compound N1C(=O)C(N)CCC2=C1C=CC1=CC=CC=C21 JUNTXRSHMXBNOU-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- 239000000741 silica gel Substances 0.000 description 8
- 229910002027 silica gel Inorganic materials 0.000 description 8
- LFKDJXLFVYVEFG-UHFFFAOYSA-N tert-butyl carbamate Chemical compound CC(C)(C)OC(N)=O LFKDJXLFVYVEFG-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 241001465754 Metazoa Species 0.000 description 7
- 229960000583 acetic acid Drugs 0.000 description 7
- 238000004440 column chromatography Methods 0.000 description 7
- 230000012010 growth Effects 0.000 description 7
- 239000012071 phase Substances 0.000 description 7
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 6
- DYNCBEBRDXRBGI-UHFFFAOYSA-N 3-azido-1,2,3,5-tetrahydrobenzo[g][1]benzazepin-4-one Chemical compound N1C(=O)C(N=[N+]=[N-])CCC2=C1C=CC1=CC=CC=C21 DYNCBEBRDXRBGI-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- 239000012362 glacial acetic acid Substances 0.000 description 6
- 238000004128 high performance liquid chromatography Methods 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- LUSMCUSTWNLKBT-UHFFFAOYSA-N 3,3-dichloro-2,5-dihydro-1h-benzo[g][1]benzazepin-4-one Chemical compound N1C(=O)C(Cl)(Cl)CCC2=C1C=CC1=CC=CC=C21 LUSMCUSTWNLKBT-UHFFFAOYSA-N 0.000 description 5
- PRRBLWWSILGWCN-UHFFFAOYSA-N 3-chloro-1,2,3,5-tetrahydrobenzo[g][1]benzazepin-4-one Chemical compound N1C(=O)C(Cl)CCC2=C1C=CC1=CC=CC=C21 PRRBLWWSILGWCN-UHFFFAOYSA-N 0.000 description 5
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 5
- 102100033367 Appetite-regulating hormone Human genes 0.000 description 5
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 5
- 241000700159 Rattus Species 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 239000000377 silicon dioxide Substances 0.000 description 5
- 230000000638 stimulation Effects 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- DFIZXEJSKKSWFD-UHFFFAOYSA-N tert-butyl n-[2-methyl-4-oxo-4-[(4-oxo-1,2,3,5-tetrahydrobenzo[g][1]benzazepin-3-yl)amino]butan-2-yl]carbamate Chemical compound N1C(=O)C(NC(=O)CC(C)(C)NC(=O)OC(C)(C)C)CCC2=C1C=CC1=CC=CC=C21 DFIZXEJSKKSWFD-UHFFFAOYSA-N 0.000 description 5
- JQFNQEHAIUGKPJ-UHFFFAOYSA-N 1,2,3,5-tetrahydrobenzo[g][1]benzazepin-4-one Chemical compound N1C(=O)CCCC2=C1C=CC1=CC=CC=C21 JQFNQEHAIUGKPJ-UHFFFAOYSA-N 0.000 description 4
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
- 206010053759 Growth retardation Diseases 0.000 description 4
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 235000011114 ammonium hydroxide Nutrition 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 108010077689 gamma-aminobutyryl-2-methyltryptophyl-2-methyltryptophyl-2-methyltryptophyl-lysinamide Proteins 0.000 description 4
- 231100000001 growth retardation Toxicity 0.000 description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 210000002966 serum Anatomy 0.000 description 4
- 235000017281 sodium acetate Nutrition 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- XGVTYZVWVYHTFY-UHFFFAOYSA-N 2-[4-[4-(bromomethyl)phenyl]thiophen-3-yl]-5-methyl-1,3,4-oxadiazole Chemical compound O1C(C)=NN=C1C1=CSC=C1C1=CC=C(CBr)C=C1 XGVTYZVWVYHTFY-UHFFFAOYSA-N 0.000 description 3
- ZWVFLNANNKAKBJ-UHFFFAOYSA-N 2-methyl-5-[4-(4-methylphenyl)thiophen-3-yl]-1,3,4-oxadiazole Chemical compound O1C(C)=NN=C1C1=CSC=C1C1=CC=C(C)C=C1 ZWVFLNANNKAKBJ-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 3
- 230000001133 acceleration Effects 0.000 description 3
- 210000004027 cell Anatomy 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
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- 239000002609 medium Substances 0.000 description 3
- ZKLJNIPOWCPKDZ-UHFFFAOYSA-N n-(3,4-dihydro-2h-phenanthren-1-ylidene)hydroxylamine Chemical compound C1=CC2=CC=CC=C2C2=C1C(=NO)CCC2 ZKLJNIPOWCPKDZ-UHFFFAOYSA-N 0.000 description 3
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- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
- BDKLKNJTMLIAFE-UHFFFAOYSA-N 2-(3-fluorophenyl)-1,3-oxazole-4-carbaldehyde Chemical compound FC1=CC=CC(C=2OC=C(C=O)N=2)=C1 BDKLKNJTMLIAFE-UHFFFAOYSA-N 0.000 description 2
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 2
- IZHVBANLECCAGF-UHFFFAOYSA-N 2-hydroxy-3-(octadecanoyloxy)propyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)COC(=O)CCCCCCCCCCCCCCCCC IZHVBANLECCAGF-UHFFFAOYSA-N 0.000 description 2
- LHJVMOIOTPJSLS-UHFFFAOYSA-N 3-methyl-3-[(2-methylpropan-2-yl)oxycarbonylamino]butanoic acid Chemical compound CC(C)(C)OC(=O)NC(C)(C)CC(O)=O LHJVMOIOTPJSLS-UHFFFAOYSA-N 0.000 description 2
- ZTFVTXDWDFIQEU-UHFFFAOYSA-N 5-[2-[4-(bromomethyl)phenyl]phenyl]-1-trityltetrazole Chemical compound C1=CC(CBr)=CC=C1C1=CC=CC=C1C1=NN=NN1C(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 ZTFVTXDWDFIQEU-UHFFFAOYSA-N 0.000 description 2
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000013222 sprague-dawley male rat Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229940037128 systemic glucocorticoids Drugs 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229960001367 tartaric acid Drugs 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 230000014616 translation Effects 0.000 description 1
- 230000032258 transport Effects 0.000 description 1
- 238000000825 ultraviolet detection Methods 0.000 description 1
- 229960003726 vasopressin Drugs 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Classifications
-
- 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
- C07D403/10—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 aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/14—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
-
- 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
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DK95294 | 1994-08-17 | ||
PCT/DK1995/000332 WO1996005195A1 (fr) | 1994-08-17 | 1995-08-17 | Nouveaux lactames naphtofusionnes a substitution n |
Publications (2)
Publication Number | Publication Date |
---|---|
NO970684D0 NO970684D0 (no) | 1997-02-14 |
NO970684L true NO970684L (no) | 1997-04-17 |
Family
ID=8099355
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO970684A NO970684L (no) | 1994-08-17 | 1997-02-14 | Nye N-substituerte naftokondenserte laktamer |
Country Status (16)
Country | Link |
---|---|
US (1) | US5817654A (fr) |
EP (1) | EP0777668A1 (fr) |
JP (1) | JPH10504293A (fr) |
CN (1) | CN1158127A (fr) |
AU (1) | AU697003B2 (fr) |
BR (1) | BR9508805A (fr) |
CA (1) | CA2196877A1 (fr) |
CZ (1) | CZ45897A3 (fr) |
HU (1) | HUT76645A (fr) |
IL (1) | IL114955A (fr) |
MX (1) | MX9701187A (fr) |
NO (1) | NO970684L (fr) |
PL (1) | PL318633A1 (fr) |
TW (1) | TW321640B (fr) |
WO (1) | WO1996005195A1 (fr) |
ZA (1) | ZA956869B (fr) |
Families Citing this family (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6211174B1 (en) | 1997-10-31 | 2001-04-03 | Merck & Co., Inc. | Naphtho-fused lactams promote release of growth hormone |
US6380184B1 (en) | 1998-10-28 | 2002-04-30 | Bristol-Myers Squibb Co. | Benzoazepines and analogs thereof useful as growth hormone secretagogues |
KR100699404B1 (ko) | 1999-02-18 | 2007-03-23 | 가켄 세야쿠 가부시키가이샤 | 성장 호르몬 분비촉진제로서의 신규 아미드 유도체 |
US6525203B1 (en) | 1999-03-12 | 2003-02-25 | Bristol-Myers Squibb Company | Heterocyclic aromatic compounds useful as growth hormone secretagogues |
US6518292B1 (en) | 1999-03-12 | 2003-02-11 | Bristol-Myers Squibb Co. | Heterocyclic aromatic compounds usefuls as growth hormone secretagogues |
BR0012202A (pt) * | 1999-06-30 | 2002-04-02 | Hamilton Civic Hospitals Res | Composições de heparina de peso molecular médio (mmwh), método de tratamento de uma condição trombótica, método de prevenção da formação de um trombo, método de inibição da formação de trombos, composição farmacêutica, método de tratamento de trombose venosa profunda, método de prevenção de embolia pulmonar, método de preparação e usos de uma composição de mmwh |
DE60115227T2 (de) | 2000-05-11 | 2006-08-24 | Bristol-Myers Squibb Co. | Tetrahydroisochinolin-analoga als wachstumshormon-sekretagoga |
AU2001291549A1 (en) * | 2000-09-08 | 2002-03-22 | Hamilton Civic Hospitals Research Development Inc. | Antithrombotic compositions |
WO2003041641A2 (fr) | 2001-11-09 | 2003-05-22 | Bristol-Myers Squibb Company | Analogues de tetrahydroisoquinoline utiles comme modulateurs de l'activite du recepteur des chimiokines |
WO2013190520A2 (fr) | 2012-06-22 | 2013-12-27 | The General Hospital Corporation | Agents de libération de gh dans le traitement d'une sténose vasculaire et d'états associés |
US9119832B2 (en) | 2014-02-05 | 2015-09-01 | The Regents Of The University Of California | Methods of treating mild brain injury |
WO2017075535A1 (fr) | 2015-10-28 | 2017-05-04 | Oxeia Biopharmaceuticals, Inc. | Méthodes de traitement de troubles neurodégénératifs |
WO2017136727A2 (fr) | 2016-02-05 | 2017-08-10 | Denali Therapeutics Inc. | Composés, compositions et procédés |
ES2912295T3 (es) | 2016-12-09 | 2022-05-25 | Denali Therapeutics Inc | Compuestos útiles como inhibidores de RIPK1 |
TW202334164A (zh) | 2022-01-12 | 2023-09-01 | 美商戴納立製藥公司 | (S)-5-苄基-N-(5-甲基-4-側氧基-2,3,4,5-四氫吡啶並[3,2-b][1,4]氧氮呯-3-基)-4H-1,2,4-三唑-3-甲醯胺的晶型 |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5206235A (en) * | 1991-03-20 | 1993-04-27 | Merck & Co., Inc. | Benzo-fused lactams that promote the release of growth hormone |
US5583130A (en) * | 1992-09-25 | 1996-12-10 | Merck & Co., Inc. | Benzo-fused lactams promote release of growth hormone |
-
1995
- 1995-08-16 IL IL11495595A patent/IL114955A/xx active IP Right Grant
- 1995-08-17 CZ CZ97458A patent/CZ45897A3/cs unknown
- 1995-08-17 JP JP8506935A patent/JPH10504293A/ja active Pending
- 1995-08-17 ZA ZA956869A patent/ZA956869B/xx unknown
- 1995-08-17 CN CN95195133A patent/CN1158127A/zh active Pending
- 1995-08-17 AU AU31618/95A patent/AU697003B2/en not_active Ceased
- 1995-08-17 PL PL95318633A patent/PL318633A1/xx unknown
- 1995-08-17 HU HU9701234A patent/HUT76645A/hu unknown
- 1995-08-17 EP EP95927662A patent/EP0777668A1/fr not_active Ceased
- 1995-08-17 CA CA002196877A patent/CA2196877A1/fr not_active Abandoned
- 1995-08-17 BR BR9508805A patent/BR9508805A/pt not_active Application Discontinuation
- 1995-08-17 MX MX9701187A patent/MX9701187A/es unknown
- 1995-08-17 WO PCT/DK1995/000332 patent/WO1996005195A1/fr not_active Application Discontinuation
- 1995-09-15 TW TW084109669A patent/TW321640B/zh active
-
1997
- 1997-01-29 US US08/790,133 patent/US5817654A/en not_active Expired - Fee Related
- 1997-02-14 NO NO970684A patent/NO970684L/no not_active Application Discontinuation
Also Published As
Publication number | Publication date |
---|---|
NO970684D0 (no) | 1997-02-14 |
PL318633A1 (en) | 1997-06-23 |
CZ45897A3 (en) | 1997-10-15 |
WO1996005195A1 (fr) | 1996-02-22 |
CA2196877A1 (fr) | 1996-02-22 |
AU3161895A (en) | 1996-03-07 |
JPH10504293A (ja) | 1998-04-28 |
HUT76645A (en) | 1997-10-28 |
BR9508805A (pt) | 1998-01-06 |
IL114955A0 (en) | 1995-12-08 |
CN1158127A (zh) | 1997-08-27 |
IL114955A (en) | 1999-12-22 |
MX9701187A (es) | 1997-05-31 |
US5817654A (en) | 1998-10-06 |
EP0777668A1 (fr) | 1997-06-11 |
AU697003B2 (en) | 1998-09-24 |
TW321640B (fr) | 1997-12-01 |
ZA956869B (en) | 1996-04-10 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
FC2A | Withdrawal, rejection or dismissal of laid open patent application |