NZ277763A - Azaheterocyclic derivatives and medicaments - Google Patents
Azaheterocyclic derivatives and medicamentsInfo
- Publication number
- NZ277763A NZ277763A NZ277763A NZ27776395A NZ277763A NZ 277763 A NZ277763 A NZ 277763A NZ 277763 A NZ277763 A NZ 277763A NZ 27776395 A NZ27776395 A NZ 27776395A NZ 277763 A NZ277763 A NZ 277763A
- Authority
- NZ
- New Zealand
- Prior art keywords
- propyl
- dibenzo
- dihydro
- carboxylic acid
- phenothiazin
- Prior art date
Links
- 239000003814 drug Substances 0.000 title claims description 24
- 150000001875 compounds Chemical class 0.000 claims abstract description 81
- 150000003839 salts Chemical class 0.000 claims abstract description 19
- 239000001257 hydrogen Substances 0.000 claims abstract description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 10
- 206010039073 rheumatoid arthritis Diseases 0.000 claims abstract description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 7
- 230000004054 inflammatory process Effects 0.000 claims abstract description 5
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 4
- 150000002367 halogens Chemical class 0.000 claims abstract description 4
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 claims abstract description 3
- 206010061218 Inflammation Diseases 0.000 claims abstract description 3
- 125000004429 atom Chemical group 0.000 claims abstract description 3
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 3
- FEQDVTZJXGQYJE-UHFFFAOYSA-N methyl 1-(3-phenothiazin-10-ylpropyl)piperidine-3-carboxylate Chemical compound C1C(C(=O)OC)CCCN1CCCN1C2=CC=CC=C2SC2=CC=CC=C21 FEQDVTZJXGQYJE-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 3
- 208000032131 Diabetic Neuropathies Diseases 0.000 claims abstract 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 30
- 239000002253 acid Substances 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 15
- 238000005160 1H NMR spectroscopy Methods 0.000 claims description 11
- 208000007920 Neurogenic Inflammation Diseases 0.000 claims description 10
- 239000003937 drug carrier Substances 0.000 claims description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims description 10
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 claims description 9
- 239000003085 diluting agent Substances 0.000 claims description 8
- OJCOPCYFLFDPTD-VEIFNGETSA-N (3r)-1-[3-(5,6-dihydrodibenzo[1,2-a:1',2'-e][7]annulen-11-ylidene)propyl]piperidine-3-carboxylic acid;hydrochloride Chemical compound Cl.C1[C@H](C(=O)O)CCCN1CCC=C1C2=CC=CC=C2CCC2=CC=CC=C21 OJCOPCYFLFDPTD-VEIFNGETSA-N 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 5
- 229950000688 phenothiazine Drugs 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- UVXXJBCXGYMTME-UHFFFAOYSA-N piperidine-1-carboxylic acid;hydrochloride Chemical compound Cl.OC(=O)N1CCCCC1 UVXXJBCXGYMTME-UHFFFAOYSA-N 0.000 claims description 3
- QGYFLHXHIUOZAZ-PKLMIRHRSA-N (3r)-1-(3-phenothiazin-10-ylpropyl)piperidine-3-carboxylic acid;hydrochloride Chemical compound Cl.C1[C@H](C(=O)O)CCCN1CCCN1C2=CC=CC=C2SC2=CC=CC=C21 QGYFLHXHIUOZAZ-PKLMIRHRSA-N 0.000 claims description 2
- LEDOSIOZONFVAQ-UHFFFAOYSA-N 1-[3-(dibenzo[1,2-a:1',2'-e][7]annulen-11-ylidene)propyl]piperidine-3-carboxylic acid Chemical compound C1C(C(=O)O)CCCN1CCC=C1C2=CC=CC=C2C=CC2=CC=CC=C21 LEDOSIOZONFVAQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- 206010012601 diabetes mellitus Diseases 0.000 claims description 2
- 201000001119 neuropathy Diseases 0.000 claims description 2
- 230000007823 neuropathy Effects 0.000 claims description 2
- 208000033808 peripheral neuropathy Diseases 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
- RXWDEUWOJGGNHU-HXUWFJFHSA-N (3r)-1-[3-(5,6-dihydrodibenzo[1,2-a:1',2'-e][7]annulen-11-ylidene)propyl]piperidine-3-carboxylic acid Chemical compound C1[C@H](C(=O)O)CCCN1CCC=C1C2=CC=CC=C2CCC2=CC=CC=C21 RXWDEUWOJGGNHU-HXUWFJFHSA-N 0.000 claims 4
- NJLAEBZVVOVDPS-UHFFFAOYSA-N hexyl 1-(3-phenothiazin-10-ylpropyl)piperidine-3-carboxylate Chemical compound C1C(C(=O)OCCCCCC)CCCN1CCCN1C2=CC=CC=C2SC2=CC=CC=C21 NJLAEBZVVOVDPS-UHFFFAOYSA-N 0.000 claims 3
- YKCVVBHYKCJTIC-MRXNPFEDSA-N (3r)-1-[3-(5-oxophenothiazin-10-yl)propyl]piperidine-3-carboxylic acid Chemical compound C1[C@H](C(=O)O)CCCN1CCCN1C2=CC=CC=C2S(=O)C2=CC=CC=C21 YKCVVBHYKCJTIC-MRXNPFEDSA-N 0.000 claims 2
- VTBYWEFVZUSBMD-MRXNPFEDSA-N (3r)-1-(3-phenothiazin-10-ylpropyl)piperidine-3-carboxylic acid Chemical compound C1[C@H](C(=O)O)CCCN1CCCN1C2=CC=CC=C2SC2=CC=CC=C21 VTBYWEFVZUSBMD-MRXNPFEDSA-N 0.000 claims 1
- AOUKABACXBPGLP-MRXNPFEDSA-N (3r)-1-(3-phenoxazin-10-ylpropyl)piperidine-3-carboxylic acid Chemical compound C1[C@H](C(=O)O)CCCN1CCCN1C2=CC=CC=C2OC2=CC=CC=C21 AOUKABACXBPGLP-MRXNPFEDSA-N 0.000 claims 1
- XJLZRTAXJOFCRE-LJQANCHMSA-N (3r)-1-[2-(5,6-dihydrobenzo[b][1]benzazepin-11-yl)ethyl]piperidine-3-carboxylic acid Chemical compound C1[C@H](C(=O)O)CCCN1CCN1C2=CC=CC=C2CCC2=CC=CC=C21 XJLZRTAXJOFCRE-LJQANCHMSA-N 0.000 claims 1
- IIMZFYZCCHOKSN-LJQANCHMSA-N (3r)-1-[3-(2-chloro-5,6-dihydrobenzo[b][1]benzazepin-11-yl)propyl]piperidine-3-carboxylic acid Chemical compound C1[C@H](C(=O)O)CCCN1CCCN1C2=CC(Cl)=CC=C2CCC2=CC=CC=C21 IIMZFYZCCHOKSN-LJQANCHMSA-N 0.000 claims 1
- OKKZSYFRRYMKIC-QGZVFWFLSA-N (3r)-1-[3-(5-methyl-6-oxobenzo[b][1,4]benzodiazepin-11-yl)propyl]piperidine-3-carboxylic acid Chemical compound C12=CC=CC=C2C(=O)N(C)C2=CC=CC=C2N1CCCN1CCC[C@@H](C(O)=O)C1 OKKZSYFRRYMKIC-QGZVFWFLSA-N 0.000 claims 1
- FWKATONZUDMDBG-UHFFFAOYSA-N 1-(3-thioxanthen-9-ylidenepropyl)piperidine-3-carboxylic acid Chemical compound C1C(C(=O)O)CCCN1CCC=C1C2=CC=CC=C2SC2=CC=CC=C21 FWKATONZUDMDBG-UHFFFAOYSA-N 0.000 claims 1
- DNUTZBZXLPWRJG-UHFFFAOYSA-N 1-Piperidine carboxylic acid Chemical compound OC(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-N 0.000 claims 1
- DTGHJYIMUYGTNH-UHFFFAOYSA-N 1-[3-(5,6-dihydrobenzo[b][1]benzazepin-11-yl)propyl]-3,6-dihydro-2h-pyridine-5-carboxylic acid Chemical compound C1C(C(=O)O)=CCCN1CCCN1C2=CC=CC=C2CCC2=CC=CC=C21 DTGHJYIMUYGTNH-UHFFFAOYSA-N 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 230000001272 neurogenic effect Effects 0.000 claims 1
- 125000005936 piperidyl group Chemical group 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 claims 1
- 239000003643 water by type Substances 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 187
- 239000000203 mixture Substances 0.000 description 118
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 111
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 111
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 109
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 84
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 84
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 75
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 72
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 71
- 239000002904 solvent Substances 0.000 description 68
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 67
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 58
- 239000000243 solution Substances 0.000 description 50
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 46
- 239000011541 reaction mixture Substances 0.000 description 46
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
- 238000010992 reflux Methods 0.000 description 45
- 239000012074 organic phase Substances 0.000 description 42
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 39
- 238000003756 stirring Methods 0.000 description 39
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 37
- 239000003921 oil Substances 0.000 description 34
- 235000019198 oils Nutrition 0.000 description 34
- 239000012071 phase Substances 0.000 description 33
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 30
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 29
- 239000000741 silica gel Substances 0.000 description 28
- 229910002027 silica gel Inorganic materials 0.000 description 28
- 239000003480 eluent Substances 0.000 description 25
- 238000004440 column chromatography Methods 0.000 description 24
- 229910052757 nitrogen Inorganic materials 0.000 description 23
- 150000002148 esters Chemical class 0.000 description 21
- 239000000047 product Substances 0.000 description 20
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- 239000007787 solid Substances 0.000 description 18
- 239000012298 atmosphere Substances 0.000 description 17
- 238000001035 drying Methods 0.000 description 17
- 238000001914 filtration Methods 0.000 description 17
- 238000001704 evaporation Methods 0.000 description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 230000008020 evaporation Effects 0.000 description 15
- 229910000027 potassium carbonate Inorganic materials 0.000 description 15
- 239000000284 extract Substances 0.000 description 14
- 238000001816 cooling Methods 0.000 description 13
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 12
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 12
- HHPGQKZOPPDLNH-OGFXRTJISA-N 2,3-dihydroxybutanedioic acid;ethyl (3r)-piperidine-3-carboxylate Chemical compound OC(=O)C(O)C(O)C(O)=O.CCOC(=O)[C@@H]1CCCNC1 HHPGQKZOPPDLNH-OGFXRTJISA-N 0.000 description 11
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 10
- 239000012267 brine Substances 0.000 description 10
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 10
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 9
- 208000002193 Pain Diseases 0.000 description 9
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 9
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 8
- 229960000583 acetic acid Drugs 0.000 description 8
- 239000012312 sodium hydride Substances 0.000 description 8
- 229910000104 sodium hydride Inorganic materials 0.000 description 8
- 239000006185 dispersion Substances 0.000 description 7
- 238000004128 high performance liquid chromatography Methods 0.000 description 7
- -1 1-substituted 4-phenyl-4-piperidinecarboxylic acid ester Chemical class 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 239000012362 glacial acetic acid Substances 0.000 description 6
- 230000014759 maintenance of location Effects 0.000 description 6
- 238000000746 purification Methods 0.000 description 6
- 150000001408 amides Chemical class 0.000 description 5
- 150000001735 carboxylic acids Chemical class 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 230000005764 inhibitory process Effects 0.000 description 5
- 230000004044 response Effects 0.000 description 5
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 4
- HJNHUFQGDJLQRS-UHFFFAOYSA-N 2-(3-bromopropoxy)oxane Chemical compound BrCCCOC1CCCCO1 HJNHUFQGDJLQRS-UHFFFAOYSA-N 0.000 description 4
- ZSMRRZONCYIFNB-UHFFFAOYSA-N 6,11-dihydro-5h-benzo[b][1]benzazepine Chemical compound C1CC2=CC=CC=C2NC2=CC=CC=C12 ZSMRRZONCYIFNB-UHFFFAOYSA-N 0.000 description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 230000001953 sensory effect Effects 0.000 description 4
- 229910000033 sodium borohydride Inorganic materials 0.000 description 4
- 239000012279 sodium borohydride Substances 0.000 description 4
- IPOVOSHRRIJKBR-UHFFFAOYSA-N 2-ethylpropanedioyl dichloride Chemical compound CCC(C(Cl)=O)C(Cl)=O IPOVOSHRRIJKBR-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-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
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
- 206010030113 Oedema Diseases 0.000 description 3
- 230000009471 action Effects 0.000 description 3
- LKXYJYDRLBPHRS-UHFFFAOYSA-N bromocyclopropane Chemical compound BrC1CC1 LKXYJYDRLBPHRS-UHFFFAOYSA-N 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000002024 ethyl acetate extract Substances 0.000 description 3
- 125000004494 ethyl ester group Chemical group 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 230000004968 inflammatory condition Effects 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- VFZXMEQGIIWBFJ-UHFFFAOYSA-M magnesium;cyclopropane;bromide Chemical compound [Mg+2].[Br-].C1C[CH-]1 VFZXMEQGIIWBFJ-UHFFFAOYSA-M 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 210000005036 nerve Anatomy 0.000 description 3
- 208000004296 neuralgia Diseases 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 108090000765 processed proteins & peptides Proteins 0.000 description 3
- 239000004089 psychotropic agent Substances 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- 239000006188 syrup Substances 0.000 description 3
- 235000020357 syrup Nutrition 0.000 description 3
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
- DLCIJMPSJTVVHJ-UHFFFAOYSA-N 10-(3-chloropropyl)phenothiazine Chemical compound C1=CC=C2N(CCCCl)C3=CC=CC=C3SC2=C1 DLCIJMPSJTVVHJ-UHFFFAOYSA-N 0.000 description 2
- UKWKPWLXOQNUGM-UHFFFAOYSA-N 10-(3-chloropropyl)phenothiazine 5-oxide Chemical compound C1=CC=C2N(CCCCl)C3=CC=CC=C3S(=O)C2=C1 UKWKPWLXOQNUGM-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
- OIUPFQXPTICAHQ-UHFFFAOYSA-N 3-(5,6-dihydrobenzo[b][1]benzazepin-11-yl)propan-1-ol Chemical compound C1CC2=CC=CC=C2N(CCCO)C2=CC=CC=C21 OIUPFQXPTICAHQ-UHFFFAOYSA-N 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- NLKSFKLPWZLDGG-UHFFFAOYSA-N 5-methyl-11h-benzo[b][1,4]benzodiazepin-6-one Chemical compound O=C1N(C)C2=CC=CC=C2NC2=CC=CC=C21 NLKSFKLPWZLDGG-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- 201000004624 Dermatitis Diseases 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- MFESCIUQSIBMSM-UHFFFAOYSA-N I-BCP Chemical compound ClCCCBr MFESCIUQSIBMSM-UHFFFAOYSA-N 0.000 description 2
- 208000019695 Migraine disease Diseases 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 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 2
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 2
- FZEYVTFCMJSGMP-UHFFFAOYSA-N acridone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3NC2=C1 FZEYVTFCMJSGMP-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 239000006286 aqueous extract Substances 0.000 description 2
- 208000006673 asthma Diseases 0.000 description 2
- 125000002843 carboxylic acid group Chemical group 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
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- BDWKVLNTCSOCCN-UHFFFAOYSA-N methyl 2-[1-[3-(5,6-dihydrobenzo[b][1]benzazepin-11-yl)propyl]pyrrolidin-3-yl]acetate Chemical compound C1C(CC(=O)OC)CCN1CCCN1C2=CC=CC=C2CCC2=CC=CC=C21 BDWKVLNTCSOCCN-UHFFFAOYSA-N 0.000 description 1
- QKONQSPVWNDJJQ-UHFFFAOYSA-N methyl 2-pyrrolidin-3-ylacetate Chemical compound COC(=O)CC1CCNC1 QKONQSPVWNDJJQ-UHFFFAOYSA-N 0.000 description 1
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- SQDFHQJTAWCFIB-UHFFFAOYSA-N n-methylidenehydroxylamine Chemical group ON=C SQDFHQJTAWCFIB-UHFFFAOYSA-N 0.000 description 1
- 210000000653 nervous system Anatomy 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 238000013421 nuclear magnetic resonance imaging Methods 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000004533 oil dispersion Substances 0.000 description 1
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- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
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- 201000000980 schizophrenia Diseases 0.000 description 1
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- 208000017520 skin disease Diseases 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000010561 standard procedure Methods 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
- C07D401/06—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 carbon chain containing only aliphatic carbon atoms
-
- 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
- A61P11/00—Drugs for disorders of the respiratory system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P23/00—Anaesthetics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/72—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D211/78—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- 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
- 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
- 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
- C07D417/06—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 linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pulmonology (AREA)
- Dermatology (AREA)
- Anesthesiology (AREA)
- Biomedical Technology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DK1994 | 1994-01-04 | ||
| DK129094 | 1994-11-09 | ||
| PCT/DK1995/000002 WO1995018793A1 (en) | 1994-01-04 | 1995-01-03 | Novel heterocyclic compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ277763A true NZ277763A (en) | 2001-11-30 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ277763A NZ277763A (en) | 1994-01-04 | 1995-01-03 | Azaheterocyclic derivatives and medicaments |
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| CN (1) | CN1083431C (enExample) |
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| AU (1) | AU691858B2 (enExample) |
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| BR (1) | BR9506452A (enExample) |
| CA (1) | CA2180238A1 (enExample) |
| CZ (1) | CZ286109B6 (enExample) |
| DE (1) | DE69516394T2 (enExample) |
| DK (1) | DK0738262T3 (enExample) |
| ES (1) | ES2147837T3 (enExample) |
| FI (1) | FI114025B (enExample) |
| GR (1) | GR3033967T3 (enExample) |
| HU (1) | HUT75878A (enExample) |
| IL (1) | IL112222A (enExample) |
| MY (1) | MY113463A (enExample) |
| NO (1) | NO306295B1 (enExample) |
| NZ (1) | NZ277763A (enExample) |
| PE (1) | PE45095A1 (enExample) |
| PL (1) | PL180209B1 (enExample) |
| PT (1) | PT738262E (enExample) |
| RU (1) | RU2167152C2 (enExample) |
| SG (1) | SG50602A1 (enExample) |
| SI (1) | SI9520023A (enExample) |
| SK (1) | SK88196A3 (enExample) |
| TW (1) | TW300887B (enExample) |
| UA (1) | UA47396C2 (enExample) |
| WO (1) | WO1995018793A1 (enExample) |
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| US6110913A (en) * | 1994-01-04 | 2000-08-29 | Novo Nordisk A/S | N-substituted azaheterocyclic carboxylic acids and esters thereof |
| US6239148B1 (en) | 1994-01-04 | 2001-05-29 | Novo Nordisk A/S | N-substituted azaheterocyclic carboxylic acids and esters thereof |
| US5698551A (en) * | 1995-04-07 | 1997-12-16 | Novo Nordisk A/S | Heterocyclic compounds |
| US5962449A (en) | 1995-04-07 | 1999-10-05 | Novo Nordisk A/S | Tricyclic compounds in treating hyperalgesic conditions and NIDDM |
| US5716949A (en) * | 1995-04-07 | 1998-02-10 | Novo Nordisk A/S | Heterocyclic compounds |
| UA54385C2 (uk) * | 1995-04-07 | 2003-03-17 | Ново Нордіск А/С | N-заміщені азагетероциклічні карбонові кислоти та їх ефіри, спосіб їх одержання, фармацевтична композиція та спосіб лікування |
| US5952352A (en) * | 1995-04-07 | 1999-09-14 | Novo Nordisk A/S | Heterocyclic compounds |
| IL124557A0 (en) * | 1995-12-15 | 1998-12-06 | Novo Nordisk As | Compositions for reducing blood glucose and/or inhibiting the activity of cgrp |
| US6323206B1 (en) | 1996-07-12 | 2001-11-27 | Millennium Pharmaceuticals, Inc. | Chemokine receptor antagonists and methods of use therefor |
| AU741839B2 (en) * | 1996-10-04 | 2001-12-13 | Novo Nordisk A/S | N-substituted azaheterocyclic compounds |
| ES2194217T3 (es) * | 1996-10-04 | 2003-11-16 | Novo Nordisk As | Spperazinas 1,4-disustituidas. |
| ZA978792B (en) * | 1996-10-04 | 1998-04-06 | Novo Nordisk As | N-substituted azaheterocyclic compounds. |
| US6040318A (en) * | 1997-06-25 | 2000-03-21 | Novo Nordisk A/S | Tricycle substituted with azaheterocyclic carboxylic acids |
| AU749505B2 (en) | 1997-10-27 | 2002-06-27 | Dr. Reddy's Laboratories Limited | Novel tricyclic compounds and their use in medicine; process for their preparation and pharmaceutical compositions containing them |
| US6509346B2 (en) | 1998-01-21 | 2003-01-21 | Millennium Pharmaceuticals, Inc. | Chemokine receptor antagonists and methods of use therefor |
| EP1047675A1 (en) * | 1998-01-21 | 2000-11-02 | Millennium Pharmaceuticals, Inc. | Chemokine receptor antagonists and methods of use therefor |
| CN1289336A (zh) | 1998-01-21 | 2001-03-28 | 千禧药品公司 | 趋化因子受体拮抗剂和其使用方法 |
| US6613905B1 (en) | 1998-01-21 | 2003-09-02 | Millennium Pharmaceuticals, Inc. | Chemokine receptor antagonists and methods of use therefor |
| ES2137136B1 (es) * | 1998-05-18 | 2000-07-01 | Esteve Labor Dr | Empleo de derivados de aril (o heteroaril) azolilcarbinoles en la elaboracion de un medicamento para el tratamiento de la inflamacion neurogenica. |
| US7271176B2 (en) * | 1998-09-04 | 2007-09-18 | Millennium Pharmaceuticals, Inc. | Chemokine receptor antagonists and methods of use thereof |
| US6468996B1 (en) * | 1998-10-21 | 2002-10-22 | Novo Nordisk A/S | Substituted hetero-polycyclic compounds as PPARα and PPARγ activators |
| EP1140084A1 (en) * | 1998-12-22 | 2001-10-10 | Novo Nordisk A/S | Novel formulation |
| US6207682B1 (en) | 1998-12-22 | 2001-03-27 | Novo Nordisk A/S | Modified release formulations containing (R)-1-(10,11-dihydro-5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1propyl)-3-piperidinecarboxylic acid |
| US7355042B2 (en) | 2001-10-16 | 2008-04-08 | Hypnion, Inc. | Treatment of CNS disorders using CNS target modulators |
| US7541365B2 (en) * | 2001-11-21 | 2009-06-02 | Millennium Pharmaceuticals, Inc. | Chemokine receptor antagonists and methods of use therefor |
| US20040087642A1 (en) * | 2002-10-24 | 2004-05-06 | Zeldis Jerome B. | Methods of using and compositions comprising a JNK inhibitor for the treatment, prevention, management and/or modification of pain |
| TWI291467B (en) * | 2002-11-13 | 2007-12-21 | Millennium Pharm Inc | CCR1 antagonists and methods of use therefor |
| US20070066570A1 (en) * | 2003-06-16 | 2007-03-22 | Michael Solomon | Methods for treating sleep disorders |
| JP2010502621A (ja) * | 2006-09-01 | 2010-01-28 | イミユーン・コントロール・インコーポレーテツド | リンパ球の活性化に関連した病気を治療するための新規な組成物および方法 |
| AR105911A1 (es) | 2015-09-03 | 2017-11-22 | Forma Therapeutics Inc | Inhibidores de hdac8 bicíclicos fusionados [6,6] |
| CA3069699A1 (en) | 2017-07-13 | 2019-01-17 | Tonix Pharmaceuticals Holding Corp. | Analogs of cyclobenzaprine and amitryptilene |
| CN115850232B (zh) * | 2023-02-16 | 2023-05-26 | 广州佳途科技股份有限公司 | 一种氟哌噻吨ep杂质h的制备方法及其应用 |
Family Cites Families (18)
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| US3316249A (en) * | 1967-04-25 | Part a.xmethyl n n-(z-diethylaminoethyl)-n-(z- nitrophenyl) anthranilate hydrochloride | ||
| US2931810A (en) * | 1960-04-05 | Phenothiazine derivatives | ||
| NL97951C (enExample) * | 1955-11-15 | |||
| NL108827C (enExample) * | 1956-04-09 | |||
| BE562299A (enExample) * | 1956-11-15 | |||
| BE560750A (enExample) * | 1957-07-26 | |||
| NL222355A (enExample) * | 1957-11-05 | |||
| FR1216268A (fr) * | 1958-04-24 | 1960-04-25 | Rhone Poulenc Sa | Nouveaux dérivés de la phénothiazine à chaîne pipéridine substituée par une fonction amide et leur préparation |
| US3069432A (en) * | 1961-02-20 | 1962-12-18 | Olin Mathieson | 5-(aminoalkyl)-5, 11-dihydrodibenzo-oxazepines |
| DE1159954B (de) * | 1961-11-25 | 1963-12-27 | Boehringer & Soehne Gmbh | Verfahren zur Herstellung neuer 10-(Alkoxypiperidinopropyl)-phenthiazine und ihrer Salze |
| US3157658A (en) * | 1963-07-05 | 1964-11-17 | Searle & Co | 1-carbalkoxy-4-(9-xanthenyl) piperazines and related compounds |
| FR145F (enExample) * | 1964-06-01 | |||
| US3886170A (en) * | 1974-04-22 | 1975-05-27 | Robins Co Inc A H | 5-(3-)SUBSTITUTED-10,11-DIHYDRO-5H-dibenz{8 b,f{9 azepines |
| US4888335A (en) * | 1988-07-25 | 1989-12-19 | Mcneilab, Inc. | 3-alkoxy-2-aminopropyl heterocyclic amines and their use as cardiovascular agents |
| US5296602A (en) * | 1991-03-18 | 1994-03-22 | Sloan-Kettering Institute For Cancer Research | Multisubstituted 1-hydroxy-9-acridones with anticancer activity |
| US5420123A (en) * | 1992-12-21 | 1995-05-30 | Bristol-Myers Squibb Company | Dibenzodiazepine endothelin antagonists |
| US5538986A (en) * | 1993-12-06 | 1996-07-23 | Schering Corporation | Tricyclic derivatives, compositions and methods of use |
| MY113463A (en) * | 1994-01-04 | 2002-03-30 | Novo Nordisk As | Novel heterocyclic compounds |
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