CA2180238A1 - Novel heterocyclic compounds - Google Patents
Novel heterocyclic compoundsInfo
- Publication number
- CA2180238A1 CA2180238A1 CA002180238A CA2180238A CA2180238A1 CA 2180238 A1 CA2180238 A1 CA 2180238A1 CA 002180238 A CA002180238 A CA 002180238A CA 2180238 A CA2180238 A CA 2180238A CA 2180238 A1 CA2180238 A1 CA 2180238A1
- Authority
- CA
- Canada
- Prior art keywords
- propyl
- dibenzo
- dihydro
- acid
- mixture
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 150000002391 heterocyclic compounds Chemical class 0.000 title 1
- 150000003839 salts Chemical class 0.000 claims abstract description 19
- 238000000034 method Methods 0.000 claims abstract description 13
- 208000007920 Neurogenic Inflammation Diseases 0.000 claims abstract description 6
- 150000001875 compounds Chemical class 0.000 claims description 47
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000003085 diluting agent Substances 0.000 claims description 5
- 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 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- OWOXYUUFFMTIPR-UHFFFAOYSA-N 2-[1-[3-(5,6-dihydrobenzo[b][1]benzazepin-11-yl)propyl]pyrrolidin-3-yl]acetic acid Chemical compound C1C(CC(=O)O)CCN1CCCN1C2=CC=CC=C2CCC2=CC=CC=C21 OWOXYUUFFMTIPR-UHFFFAOYSA-N 0.000 claims description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 2
- 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 2
- SJJUKGVRGZOKFH-MRXNPFEDSA-N (3r)-1-(3-fluoren-9-ylidenepropyl)piperidine-3-carboxylic acid Chemical compound C1[C@H](C(=O)O)CCCN1CCC=C1C2=CC=CC=C2C2=CC=CC=C21 SJJUKGVRGZOKFH-MRXNPFEDSA-N 0.000 claims 1
- 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
- YZPGLTDLJQQMER-OAQYLSRUSA-N (3r)-1-[3-(2-methyl-5,6-dihydrodibenzo[1,2-e:1',2'-f][7]annulen-11-ylidene)propyl]piperidine-3-carboxylic acid Chemical compound C12=CC(C)=CC=C2CCC2=CC=CC=C2C1=CCCN1CCC[C@@H](C(O)=O)C1 YZPGLTDLJQQMER-OAQYLSRUSA-N 0.000 claims 1
- 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 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
- 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 1
- IBGRWNINCPSXHG-QGZVFWFLSA-N (3r)-1-[3-(6h-benzo[c][1,5]benzoxazepin-11-yl)propyl]piperidine-3-carboxylic acid Chemical compound C1[C@H](C(=O)O)CCCN1CCCN1C2=CC=CC=C2OCC2=CC=CC=C21 IBGRWNINCPSXHG-QGZVFWFLSA-N 0.000 claims 1
- RXWDEUWOJGGNHU-FQEVSTJZSA-N (3s)-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-FQEVSTJZSA-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
- 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
- HIAVZZYGFRWZNI-UHFFFAOYSA-N 1-[3-(5,6-dihydrodibenzo[1,2-a:1',2'-e][7]annulen-11-ylidene)propyl]-3,6-dihydro-2h-pyridine-5-carboxylic acid Chemical compound C1C(C(=O)O)=CCCN1CCC=C1C2=CC=CC=C2CCC2=CC=CC=C21 HIAVZZYGFRWZNI-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 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 1
- 230000001225 therapeutic effect Effects 0.000 claims 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 141
- 150000002148 esters Chemical class 0.000 abstract description 21
- 208000004296 neuralgia Diseases 0.000 abstract description 4
- 230000000917 hyperalgesic effect Effects 0.000 abstract description 3
- 230000004054 inflammatory process Effects 0.000 abstract description 3
- 210000001170 unmyelinated nerve fiber Anatomy 0.000 abstract description 3
- 230000004968 inflammatory condition Effects 0.000 abstract description 2
- 230000001991 pathophysiological effect Effects 0.000 abstract description 2
- 238000002360 preparation method Methods 0.000 abstract description 2
- 125000000547 substituted alkyl group Chemical group 0.000 abstract description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 106
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 96
- 229910001868 water Inorganic materials 0.000 description 90
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 87
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 76
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 76
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 72
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 68
- 239000002904 solvent Substances 0.000 description 67
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 56
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 50
- 239000000243 solution Substances 0.000 description 48
- 238000010992 reflux Methods 0.000 description 44
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 41
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 39
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 39
- 235000019341 magnesium sulphate Nutrition 0.000 description 38
- 238000003756 stirring Methods 0.000 description 38
- 239000002253 acid Substances 0.000 description 37
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 36
- 239000003921 oil Substances 0.000 description 36
- 235000019198 oils Nutrition 0.000 description 36
- 239000012071 phase Substances 0.000 description 33
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 30
- 229910052681 coesite Inorganic materials 0.000 description 28
- 229910052906 cristobalite Inorganic materials 0.000 description 28
- 239000000741 silica gel Substances 0.000 description 28
- 229910002027 silica gel Inorganic materials 0.000 description 28
- 239000000377 silicon dioxide Substances 0.000 description 28
- 235000012239 silicon dioxide Nutrition 0.000 description 28
- 229910052682 stishovite Inorganic materials 0.000 description 28
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 28
- 229910052905 tridymite Inorganic materials 0.000 description 28
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 27
- 239000003480 eluent Substances 0.000 description 25
- 239000012074 organic phase Substances 0.000 description 25
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 22
- 239000000047 product Substances 0.000 description 20
- 239000011541 reaction mixture Substances 0.000 description 19
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- 239000007787 solid Substances 0.000 description 18
- 238000001035 drying Methods 0.000 description 17
- 235000019439 ethyl acetate Nutrition 0.000 description 15
- 125000004494 ethyl ester group Chemical group 0.000 description 15
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 14
- 125000003963 dichloro group Chemical group Cl* 0.000 description 13
- 229940093499 ethyl acetate Drugs 0.000 description 13
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 238000001816 cooling Methods 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- -1 1-substituted 4-phenyl-4-piperidinecarboxylic acid ester Chemical class 0.000 description 10
- 238000005160 1H NMR spectroscopy Methods 0.000 description 10
- 241000282320 Panthera leo Species 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 9
- 208000002193 Pain Diseases 0.000 description 9
- 239000012267 brine Substances 0.000 description 9
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 9
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 8
- 239000007832 Na2SO4 Substances 0.000 description 8
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 8
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 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
- 229910052938 sodium sulfate Inorganic materials 0.000 description 8
- 235000011152 sodium sulphate Nutrition 0.000 description 8
- 238000004128 high performance liquid chromatography Methods 0.000 description 7
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000012362 glacial acetic acid Substances 0.000 description 6
- LUMNWCHHXDUKFI-UHFFFAOYSA-N 5-bicyclo[2.2.1]hept-2-enylmethanol Chemical compound C1C2C(CO)CC1C=C2 LUMNWCHHXDUKFI-UHFFFAOYSA-N 0.000 description 5
- 150000001408 amides Chemical class 0.000 description 5
- 150000001735 carboxylic acids Chemical class 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- XIWBSOUNZWSFKU-SSDOTTSWSA-N ethyl (3r)-piperidine-3-carboxylate Chemical compound CCOC(=O)[C@@H]1CCCNC1 XIWBSOUNZWSFKU-SSDOTTSWSA-N 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 239000003112 inhibitor Substances 0.000 description 5
- 230000005764 inhibitory process Effects 0.000 description 5
- 229940093956 potassium carbonate Drugs 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- 241001657788 Orya Species 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- PJFXDPZWCVXNQZ-UHFFFAOYSA-N ethyl 3-oxo-1,2-dihydropyrazole-4-carboxylate Chemical group CCOC(=O)C1=CNNC1=O PJFXDPZWCVXNQZ-UHFFFAOYSA-N 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 150000002500 ions Chemical class 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 230000004044 response Effects 0.000 description 4
- 230000001953 sensory effect Effects 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 239000012279 sodium borohydride Substances 0.000 description 4
- 229910000033 sodium borohydride Inorganic materials 0.000 description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 3
- 230000009471 action Effects 0.000 description 3
- XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 229960003692 gamma aminobutyric acid Drugs 0.000 description 3
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 3
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 3
- 210000005036 nerve Anatomy 0.000 description 3
- 235000011181 potassium carbonates Nutrition 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 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
- BDERNNFJNOPAEC-UHFFFAOYSA-N 1-propanol Substances CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- HJNHUFQGDJLQRS-UHFFFAOYSA-N 2-(3-bromopropoxy)oxane Chemical compound BrCCCOC1CCCCO1 HJNHUFQGDJLQRS-UHFFFAOYSA-N 0.000 description 2
- IPOVOSHRRIJKBR-UHFFFAOYSA-N 2-ethylpropanedioyl dichloride Chemical compound CCC(C(Cl)=O)C(Cl)=O IPOVOSHRRIJKBR-UHFFFAOYSA-N 0.000 description 2
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 2
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- 241000283986 Lepus Species 0.000 description 2
- 229910010084 LiAlH4 Inorganic materials 0.000 description 2
- 241001465754 Metazoa Species 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
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 229960001040 ammonium chloride Drugs 0.000 description 2
- 125000002843 carboxylic acid group Chemical group 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000001684 chronic effect Effects 0.000 description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 210000002683 foot Anatomy 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- 125000003976 glyceryl group Chemical group [H]C([*])([H])C(O[H])([H])C(O[H])([H])[H] 0.000 description 2
- 230000028709 inflammatory response Effects 0.000 description 2
- 239000012280 lithium aluminium hydride Substances 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 235000001055 magnesium Nutrition 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 206010027599 migraine Diseases 0.000 description 2
- 230000001272 neurogenic effect Effects 0.000 description 2
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Classifications
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- 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
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
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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
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- 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
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- 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
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- 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
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
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- Pain & Pain Management (AREA)
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- Anesthesiology (AREA)
- Pulmonology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Rheumatology (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 (4)
| Application Number | Priority Date | Filing Date | Title |
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| DK0019/94 | 1994-01-04 | ||
| DK1994 | 1994-01-04 | ||
| DK1290/94 | 1994-11-09 | ||
| DK129094 | 1994-11-09 |
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|---|---|
| CA2180238A1 true CA2180238A1 (en) | 1995-07-13 |
Family
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| CA002180238A Abandoned CA2180238A1 (en) | 1994-01-04 | 1995-01-03 | Novel heterocyclic compounds |
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| AT (1) | ATE191909T1 (enExample) |
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| BG (1) | BG100692A (enExample) |
| 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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| Publication number | Priority date | Publication date | Assignee | Title |
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| US6239148B1 (en) | 1994-01-04 | 2001-05-29 | Novo Nordisk A/S | N-substituted azaheterocyclic carboxylic acids and esters thereof |
| MY113463A (en) * | 1994-01-04 | 2002-03-30 | Novo Nordisk As | Novel heterocyclic compounds |
| US6110913A (en) * | 1994-01-04 | 2000-08-29 | Novo Nordisk A/S | N-substituted azaheterocyclic carboxylic acids and esters thereof |
| US5716949A (en) * | 1995-04-07 | 1998-02-10 | Novo Nordisk A/S | Heterocyclic compounds |
| US5952352A (en) * | 1995-04-07 | 1999-09-14 | 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 |
| 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 |
| US5698551A (en) * | 1995-04-07 | 1997-12-16 | Novo Nordisk A/S | Heterocyclic compounds |
| KR20000064411A (ko) | 1995-12-15 | 2000-11-06 | 한센 핀 베네드, 안네 제헤르, 웨이콥 마리안느 | 새로운방법 |
| US6323206B1 (en) | 1996-07-12 | 2001-11-27 | Millennium Pharmaceuticals, Inc. | Chemokine receptor antagonists and methods of use therefor |
| HUP0000088A3 (en) * | 1996-10-04 | 2000-09-28 | Novo Nordisk As | N-substituted azaheterocyclic compounds, process for producing them and pharmaceutical compositions containing them |
| ZA978792B (en) * | 1996-10-04 | 1998-04-06 | Novo Nordisk As | N-substituted azaheterocyclic compounds. |
| KR20000048899A (ko) * | 1996-10-04 | 2000-07-25 | 한센 핀 베네드, 안네 제헤르, 웨이콥 마리안느 | 1,4-디치환 피페라진 |
| US6040318A (en) * | 1997-06-25 | 2000-03-21 | Novo Nordisk A/S | Tricycle substituted with azaheterocyclic carboxylic acids |
| EP1049684A1 (en) | 1997-10-27 | 2000-11-08 | Dr. Reddy's Research Foundation | Novel tricyclic compounds and their use in medicine; process for their preparation and pharmaceutical compositions containing them |
| CA2319077A1 (en) | 1998-01-21 | 1999-07-29 | Yoshisuke Nakasato | Chemokine receptor antagonists and methods of use therefor |
| US6613905B1 (en) | 1998-01-21 | 2003-09-02 | Millennium Pharmaceuticals, Inc. | Chemokine receptor antagonists and methods of use therefor |
| US6509346B2 (en) | 1998-01-21 | 2003-01-21 | Millennium Pharmaceuticals, Inc. | Chemokine receptor antagonists and methods of use therefor |
| JP2002501052A (ja) * | 1998-01-21 | 2002-01-15 | ミレニアム・ファーマシューティカルズ・インコーポレイテッド | ケモカイン受容体アンタゴニストおよびその使用方法 |
| 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 |
| AU2007290386A1 (en) | 2006-09-01 | 2008-03-06 | Immune Control, Inc. | Novel compositions and methods for treatment of diseases related to activated lymphocytes |
| US10029995B2 (en) | 2015-09-03 | 2018-07-24 | Forma Therapeutics, Inc. | [6,6] fused bicyclic HDAC8 inhibitors |
| EP3651751A4 (en) | 2017-07-13 | 2021-03-31 | Tonix Pharmaceuticals Holding Corp. | CYCLOBENZAPRINE AND AMITRYPTILENE ANALOGUES |
| 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 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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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 | ||
| BE552557A (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 |
-
1994
- 1994-12-30 MY MYPI94003583A patent/MY113463A/en unknown
-
1995
- 1995-01-02 IL IL11222295A patent/IL112222A/xx not_active IP Right Cessation
- 1995-01-03 US US08/367,648 patent/US5595989A/en not_active Expired - Fee Related
- 1995-01-03 AT AT95904409T patent/ATE191909T1/de not_active IP Right Cessation
- 1995-01-03 BR BR9506452A patent/BR9506452A/pt not_active IP Right Cessation
- 1995-01-03 HU HU9601842A patent/HUT75878A/hu unknown
- 1995-01-03 SK SK881-96A patent/SK88196A3/sk unknown
- 1995-01-03 SG SG1996006195A patent/SG50602A1/en unknown
- 1995-01-03 PT PT95904409T patent/PT738262E/pt unknown
- 1995-01-03 DE DE69516394T patent/DE69516394T2/de not_active Expired - Fee Related
- 1995-01-03 KR KR1019960703605A patent/KR100329450B1/ko not_active Expired - Fee Related
- 1995-01-03 ES ES95904409T patent/ES2147837T3/es not_active Expired - Lifetime
- 1995-01-03 CN CN95191845A patent/CN1083431C/zh not_active Expired - Fee Related
- 1995-01-03 PL PL95315294A patent/PL180209B1/pl not_active IP Right Cessation
- 1995-01-03 JP JP7518275A patent/JP2944221B2/ja not_active Expired - Fee Related
- 1995-01-03 CZ CZ19961921A patent/CZ286109B6/cs unknown
- 1995-01-03 SI SI9520023A patent/SI9520023A/sl unknown
- 1995-01-03 NZ NZ277763A patent/NZ277763A/en unknown
- 1995-01-03 WO PCT/DK1995/000002 patent/WO1995018793A1/en not_active Ceased
- 1995-01-03 CA CA002180238A patent/CA2180238A1/en not_active Abandoned
- 1995-01-03 RU RU96116134/04A patent/RU2167152C2/ru not_active IP Right Cessation
- 1995-01-03 DK DK95904409T patent/DK0738262T3/da active
- 1995-01-03 UA UA96072659A patent/UA47396C2/uk unknown
- 1995-01-03 AU AU13110/95A patent/AU691858B2/en not_active Ceased
- 1995-01-03 EP EP95904409A patent/EP0738262B1/en not_active Expired - Lifetime
- 1995-01-04 PE PE1995258527A patent/PE45095A1/es not_active Application Discontinuation
- 1995-02-22 TW TW084101613A patent/TW300887B/zh active
- 1995-05-18 US US08/444,140 patent/US5688788A/en not_active Expired - Fee Related
- 1995-10-18 US US08/544,500 patent/US5721254A/en not_active Expired - Fee Related
- 1995-10-18 US US08/544,682 patent/US5795888A/en not_active Expired - Fee Related
- 1995-10-18 US US08/544,502 patent/US5693649A/en not_active Expired - Fee Related
- 1995-10-18 US US08/544,905 patent/US5712292A/en not_active Expired - Fee Related
-
1996
- 1996-03-27 US US08/626,745 patent/US5668129A/en not_active Expired - Fee Related
- 1996-07-02 BG BG100692A patent/BG100692A/xx unknown
- 1996-07-03 NO NO962811A patent/NO306295B1/no not_active IP Right Cessation
- 1996-07-04 FI FI962749A patent/FI114025B/fi active
-
1998
- 1998-01-23 US US09/012,918 patent/US6043239A/en not_active Expired - Fee Related
-
2000
- 2000-07-17 GR GR20000401652T patent/GR3033967T3/el not_active IP Right Cessation
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Legal Events
| Date | Code | Title | Description |
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| EEER | Examination request | ||
| FZDE | Discontinued | ||
| FZDE | Discontinued |
Effective date: 20061027 |