UA67717C2 - 3-acylindoles and pharmaceutical composition based thereon - Google Patents
3-acylindoles and pharmaceutical composition based thereon Download PDFInfo
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- UA67717C2 UA67717C2 UA97126177A UA97126177A UA67717C2 UA 67717 C2 UA67717 C2 UA 67717C2 UA 97126177 A UA97126177 A UA 97126177A UA 97126177 A UA97126177 A UA 97126177A UA 67717 C2 UA67717 C2 UA 67717C2
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- Ukraine
- Prior art keywords
- group
- methyl
- hydrogen
- formula
- halogen
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- 239000008194 pharmaceutical composition Substances 0.000 title claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 46
- 239000001257 hydrogen Substances 0.000 claims abstract description 46
- -1 1,2,3,4-tetrahydronaphth-1-yl Chemical group 0.000 claims abstract description 42
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 25
- 150000002367 halogens Chemical class 0.000 claims abstract description 24
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 22
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims abstract description 15
- 125000001424 substituent group Chemical group 0.000 claims abstract description 9
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 8
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims abstract description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 4
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims abstract description 3
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims abstract description 3
- 125000004534 benzothien-2-yl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims abstract description 3
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims abstract description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 183
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- 125000004414 alkyl thio group Chemical group 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 12
- 239000000460 chlorine Substances 0.000 claims description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- PZDKOIGGKPUBPS-UHFFFAOYSA-N (4-bromonaphthalen-1-yl)-(7-fluoro-2-methyl-1-pentylindol-3-yl)methanone Chemical compound C12=CC=CC(F)=C2N(CCCCC)C(C)=C1C(=O)C1=CC=C(Br)C2=CC=CC=C12 PZDKOIGGKPUBPS-UHFFFAOYSA-N 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- HHRJMNLXWZXMMK-UHFFFAOYSA-N (4-bromonaphthalen-1-yl)-(7-methoxy-2-methyl-1-pentylindol-3-yl)methanone Chemical compound C12=CC=CC(OC)=C2N(CCCCC)C(C)=C1C(=O)C1=CC=C(Br)C2=CC=CC=C12 HHRJMNLXWZXMMK-UHFFFAOYSA-N 0.000 claims description 4
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 4
- 229910052700 potassium Inorganic materials 0.000 claims description 4
- XQLGZJHGMVZVJE-UHFFFAOYSA-N (4-chloronaphthalen-1-yl)-(7-methoxy-2-methyl-1-pentylindol-3-yl)methanone Chemical group C12=CC=CC(OC)=C2N(CCCCC)C(C)=C1C(=O)C1=CC=C(Cl)C2=CC=CC=C12 XQLGZJHGMVZVJE-UHFFFAOYSA-N 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 1
- 238000012876 topography Methods 0.000 claims 1
- 239000000556 agonist Substances 0.000 abstract description 12
- 229910052799 carbon Inorganic materials 0.000 abstract description 4
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract description 4
- 125000005843 halogen group Chemical group 0.000 abstract description 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 abstract description 3
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 abstract description 3
- 125000004197 benzothien-3-yl group Chemical group [H]C1=C(*)C2=C([H])C([H])=C([H])C([H])=C2S1 0.000 abstract description 2
- 229940124622 immune-modulator drug Drugs 0.000 abstract description 2
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 abstract description 2
- 125000001041 indolyl group Chemical group 0.000 abstract description 2
- 125000004430 oxygen atom Chemical group O* 0.000 abstract description 2
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 abstract description 2
- 125000004571 thiomorpholin-4-yl group Chemical group N1(CCSCC1)* 0.000 abstract description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 8
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 2
- 125000003367 polycyclic group Chemical group 0.000 abstract 2
- 101000875075 Homo sapiens Cannabinoid receptor 2 Proteins 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 102000056693 human CNR2 Human genes 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 83
- 238000000034 method Methods 0.000 description 72
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 56
- 239000000243 solution Substances 0.000 description 51
- 239000000203 mixture Substances 0.000 description 46
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 37
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 35
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 35
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 34
- 238000006243 chemical reaction Methods 0.000 description 29
- 239000002904 solvent Substances 0.000 description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
- 102000005962 receptors Human genes 0.000 description 26
- 108020003175 receptors Proteins 0.000 description 26
- 102000018208 Cannabinoid Receptor Human genes 0.000 description 22
- 108050007331 Cannabinoid receptor Proteins 0.000 description 22
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 21
- 239000000047 product Substances 0.000 description 21
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 19
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 18
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 18
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 18
- 239000000741 silica gel Substances 0.000 description 18
- 229910002027 silica gel Inorganic materials 0.000 description 18
- 238000004587 chromatography analysis Methods 0.000 description 17
- 241000282414 Homo sapiens Species 0.000 description 16
- 230000015572 biosynthetic process Effects 0.000 description 16
- 239000003480 eluent Substances 0.000 description 15
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 14
- 239000012074 organic phase Substances 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 238000005917 acylation reaction Methods 0.000 description 12
- 150000002475 indoles Chemical class 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 12
- 125000006530 (C4-C6) alkyl group Chemical group 0.000 description 11
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 11
- 239000013067 intermediate product Substances 0.000 description 11
- 230000010933 acylation Effects 0.000 description 10
- 239000002585 base Substances 0.000 description 10
- 239000003960 organic solvent Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 229920006395 saturated elastomer Polymers 0.000 description 9
- 239000012047 saturated solution Substances 0.000 description 9
- 238000009835 boiling Methods 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 7
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 7
- 239000012442 inert solvent Substances 0.000 description 7
- 230000005764 inhibitory process Effects 0.000 description 7
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 229930003827 cannabinoid Natural products 0.000 description 6
- 239000003557 cannabinoid Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical compound C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 5
- 229940054051 antipsychotic indole derivative Drugs 0.000 description 5
- 229940065144 cannabinoids Drugs 0.000 description 5
- 210000004027 cell Anatomy 0.000 description 5
- 201000010099 disease Diseases 0.000 description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
- 150000004820 halides Chemical class 0.000 description 5
- 239000005457 ice water Substances 0.000 description 5
- 230000002262 irrigation Effects 0.000 description 5
- 238000003973 irrigation Methods 0.000 description 5
- 150000002576 ketones Chemical class 0.000 description 5
- 239000012312 sodium hydride Substances 0.000 description 5
- 229910000104 sodium hydride Inorganic materials 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000002841 Lewis acid Substances 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 150000007517 lewis acids Chemical class 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 125000001624 naphthyl group Chemical group 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 238000007363 ring formation reaction Methods 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- NBOMNTLFRHMDEZ-UHFFFAOYSA-N thiosalicylic acid Chemical compound OC(=O)C1=CC=CC=C1S NBOMNTLFRHMDEZ-UHFFFAOYSA-N 0.000 description 4
- BLXSFCHWMBESKV-UHFFFAOYSA-N 1-iodopentane Chemical compound CCCCCI BLXSFCHWMBESKV-UHFFFAOYSA-N 0.000 description 3
- JCUIMURERROQTR-UHFFFAOYSA-N 4-bromonaphthalene-1-carbonyl chloride Chemical compound C1=CC=C2C(C(=O)Cl)=CC=C(Br)C2=C1 JCUIMURERROQTR-UHFFFAOYSA-N 0.000 description 3
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 3
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- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
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- 229910000564 Raney nickel Inorganic materials 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
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- FSRGZKUMFXNDAR-UHFFFAOYSA-N methanesulfonic acid;[3-(2-morpholin-4-ylethyl)indol-1-yl]-naphthalen-1-ylmethanone Chemical compound CS(O)(=O)=O.C=1C=CC2=CC=CC=C2C=1C(=O)N(C1=CC=CC=C11)C=C1CCN1CCOCC1 FSRGZKUMFXNDAR-UHFFFAOYSA-N 0.000 description 3
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- OKLQXZSFLXZPLW-UHFFFAOYSA-N (4-bromonaphthalen-1-yl)-[7-methoxy-2-methyl-1-(2-morpholin-4-ylethyl)indol-3-yl]methanone Chemical compound C1=2C(OC)=CC=CC=2C(C(=O)C=2C3=CC=CC=C3C(Br)=CC=2)=C(C)N1CCN1CCOCC1 OKLQXZSFLXZPLW-UHFFFAOYSA-N 0.000 description 2
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 2
- MNCMBBIFTVWHIP-UHFFFAOYSA-N 1-anthracen-9-yl-2,2,2-trifluoroethanone Chemical group C1=CC=C2C(C(=O)C(F)(F)F)=C(C=CC=C3)C3=CC2=C1 MNCMBBIFTVWHIP-UHFFFAOYSA-N 0.000 description 2
- MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 description 2
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- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
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- 238000010908 decantation Methods 0.000 description 2
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- UAIZDWNSWGTKFZ-UHFFFAOYSA-L ethylaluminum(2+);dichloride Chemical compound CC[Al](Cl)Cl UAIZDWNSWGTKFZ-UHFFFAOYSA-L 0.000 description 2
- 235000003599 food sweetener Nutrition 0.000 description 2
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- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 2
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- SETMGIIITGNLAS-UHFFFAOYSA-N spizofurone Chemical compound O=C1C2=CC(C(=O)C)=CC=C2OC21CC2 SETMGIIITGNLAS-UHFFFAOYSA-N 0.000 description 1
- 229950001870 spizofurone Drugs 0.000 description 1
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Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
- A61K31/404—Indoles, e.g. pindolol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5355—Non-condensed oxazines and containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/538—1,4-Oxazines, e.g. morpholine ortho- or peri-condensed with carbocyclic ring systems
-
- 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]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- 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
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/12—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- Pain & Pain Management (AREA)
- Pulmonology (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9507438A FR2735774B1 (fr) | 1995-06-21 | 1995-06-21 | Utilisation de composes agonistes du recepteur cb2 humain pour la preparation de medicaments immunomodulateurs, nouveaux composes agonistes du recepteur cb2 et les compositions pharmaceutiques les contenant |
| PCT/FR1996/000959 WO1997000860A1 (fr) | 1995-06-21 | 1996-06-20 | Composes agonistes du recepteur cb¿2? |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UA67717C2 true UA67717C2 (en) | 2004-07-15 |
Family
ID=9480236
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UA97126177A UA67717C2 (en) | 1995-06-21 | 1996-06-20 | 3-acylindoles and pharmaceutical composition based thereon |
Country Status (30)
| Country | Link |
|---|---|
| US (1) | US6013648A (et) |
| EP (1) | EP0833818B1 (et) |
| JP (1) | JP3417566B2 (et) |
| KR (1) | KR19990028272A (et) |
| CN (1) | CN1150166C (et) |
| AT (1) | ATE207054T1 (et) |
| AU (1) | AU717858B2 (et) |
| BR (1) | BR9608640A (et) |
| CA (1) | CA2225379A1 (et) |
| CZ (1) | CZ292630B6 (et) |
| DE (1) | DE69616056T2 (et) |
| DK (1) | DK0833818T3 (et) |
| EE (1) | EE9700345A (et) |
| ES (1) | ES2165986T3 (et) |
| FR (1) | FR2735774B1 (et) |
| HK (1) | HK1005093A1 (et) |
| HU (1) | HUP9900019A3 (et) |
| IL (1) | IL122637A0 (et) |
| IS (1) | IS4637A (et) |
| MX (1) | MX9710251A (et) |
| NO (1) | NO975989L (et) |
| NZ (1) | NZ312161A (et) |
| PL (1) | PL185598B1 (et) |
| PT (1) | PT833818E (et) |
| RU (1) | RU2200736C2 (et) |
| SI (1) | SI0833818T1 (et) |
| SK (1) | SK283660B6 (et) |
| TR (1) | TR199701660T1 (et) |
| UA (1) | UA67717C2 (et) |
| WO (1) | WO1997000860A1 (et) |
Families Citing this family (85)
| Publication number | Priority date | Publication date | Assignee | Title |
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| FR2735774B1 (fr) * | 1995-06-21 | 1997-09-12 | Sanofi Sa | Utilisation de composes agonistes du recepteur cb2 humain pour la preparation de medicaments immunomodulateurs, nouveaux composes agonistes du recepteur cb2 et les compositions pharmaceutiques les contenant |
| EP1075470B1 (en) * | 1998-05-04 | 2003-08-13 | The University Of Connecticut | Novel analgesic and immunomodulatory cannabinoids |
| WO1999057107A2 (en) * | 1998-05-04 | 1999-11-11 | The University Of Connecticut | Cannabinoids selective for the cb2 receptor |
| US7589220B2 (en) | 1998-06-09 | 2009-09-15 | University Of Connecticut | Inhibitors of the anandamide transporter |
| US7897598B2 (en) | 1998-06-09 | 2011-03-01 | Alexandros Makriyannis | Inhibitors of the anandamide transporter |
| DE19837627A1 (de) * | 1998-08-19 | 2000-02-24 | Bayer Ag | Neue Aminosäureester von Arylsulfonamiden und Analoga |
| US7276613B1 (en) | 1998-11-24 | 2007-10-02 | University Of Connecticut | Retro-anandamides, high affinity and stability cannabinoid receptor ligands |
| US7161016B1 (en) | 1998-11-24 | 2007-01-09 | University Of Connecticut | Cannabimimetic lipid amides as useful medications |
| US6566560B2 (en) | 1999-03-22 | 2003-05-20 | Immugen Pharmaceuticals, Inc. | Resorcinolic compounds |
| GB9923314D0 (en) * | 1999-10-01 | 1999-12-08 | Pfizer Ltd | Acylation process |
| WO2001028557A1 (en) * | 1999-10-18 | 2001-04-26 | University Of Connecticut | Cannabimimetic indole derivatives |
| US7393842B2 (en) | 2001-08-31 | 2008-07-01 | University Of Connecticut | Pyrazole analogs acting on cannabinoid receptors |
| EP1702617A1 (en) * | 1999-10-18 | 2006-09-20 | The University Of Connecticut | Cannabimimetic indole derivatives |
| US7119108B1 (en) | 1999-10-18 | 2006-10-10 | University Of Connecticut | Pyrazole derivatives as cannabinoid receptor antagonists |
| US8084467B2 (en) | 1999-10-18 | 2011-12-27 | University Of Connecticut | Pyrazole derivatives as cannabinoid receptor antagonists |
| AU778159B2 (en) | 1999-10-18 | 2004-11-18 | University Of Connecticut, The | Peripheral cannabinoid receptor (CB2) selective ligands |
| US7741365B2 (en) | 1999-10-18 | 2010-06-22 | University Of Connecticut | Peripheral cannabinoid receptor (CB2) selective ligands |
| US6943266B1 (en) * | 1999-10-18 | 2005-09-13 | University Of Connecticut | Bicyclic cannabinoid agonists for the cannabinoid receptor |
| US6900236B1 (en) | 1999-10-18 | 2005-05-31 | University Of Connecticut | Cannabimimetic indole derivatives |
| IL132661A (en) | 1999-10-31 | 2008-11-26 | Raphael Mechoulam | Agonists specific for peripheral cannabinoid receptors |
| JP2004502642A (ja) * | 2000-02-11 | 2004-01-29 | ブリストル−マイヤーズ スクイブ カンパニー | カンナビノイドレセプターモジュレーター、それらの製造方法、および呼吸系および非呼吸系疾患の処置のためのカンナビノイドレセプターモジュレーターの使用 |
| JP2003534298A (ja) * | 2000-05-23 | 2003-11-18 | ザ・リージェンツ・オブ・ザ・ユニバーシティー・オブ・カリフォルニア | 咳の新規治療法 |
| EP1305285B1 (en) | 2000-07-25 | 2007-05-16 | Merck & Co., Inc. | N-substituted indoles useful in the treatment of diabetes |
| US6541510B2 (en) * | 2000-09-28 | 2003-04-01 | Immugen Pharmaceuticals, Inc. | Antiviral methods and compounds |
| US20020137802A1 (en) * | 2000-09-28 | 2002-09-26 | Travis Craig R. | Methods and compounds for inhibiting eicosanoid metabolism and platelet aggregation |
| FR2814678B1 (fr) * | 2000-10-04 | 2002-12-20 | Aventis Pharma Sa | Association d'un antagoniste du recepteur cb1 et de sibutramine, les compositions pharmaceutiques les contenant et leur utilisation pour la traitement de l'obesite |
| AUPR118000A0 (en) * | 2000-11-02 | 2000-11-23 | Amrad Operations Pty. Limited | Therapeutic molecules and methods |
| FR2816938B1 (fr) * | 2000-11-22 | 2003-01-03 | Sanofi Synthelabo | Derives de 3-aroylindole, leur procede de preparation et les compositions pharmaceutiques en contenant |
| WO2002058636A2 (en) | 2001-01-26 | 2002-08-01 | University Of Connecticut | Novel cannabimimetic ligands |
| JP2005503998A (ja) | 2001-01-29 | 2005-02-10 | ユニバーシティ オブ コネチカット | 受容体選択性のカンナビミメティックアミノアルキルインドール |
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| JP4312594B2 (ja) | 2001-07-13 | 2009-08-12 | ユニバーシティ オブ コネチカット | 新規な二環式及び三環式カンナビノイド |
| DE60228713D1 (de) * | 2001-07-18 | 2008-10-16 | Unilever Nv | Zusammensetzungen für die behandlung von haaren und/oder kopfhaut |
| CN1589269A (zh) | 2001-10-26 | 2005-03-02 | 康涅狄格大学 | 杂1,2－二氢化茚:一类新型有效的大麻配体 |
| BR0214164A (pt) * | 2001-11-14 | 2004-09-28 | Schering Corp | Ligantes do receptor canabinóide |
| TW200407110A (en) * | 2001-11-23 | 2004-05-16 | Astrazeneca Ab | New use for the treatment of gastroesophageal reflux disease |
| WO2003049727A1 (en) * | 2001-12-07 | 2003-06-19 | Virginia Commonwealth University | Treatment of neoplasia |
| US6933316B2 (en) * | 2001-12-13 | 2005-08-23 | National Health Research Institutes | Indole compounds |
| US7632955B2 (en) * | 2001-12-13 | 2009-12-15 | National Health Research Institutes | Indole compounds |
| US7528165B2 (en) * | 2001-12-13 | 2009-05-05 | National Health Research Institutes | Indole compounds |
| US20040171613A1 (en) * | 2001-12-27 | 2004-09-02 | Japan Tobacco Inc. | Therapeutic agent for non-immediate type allergic diseases |
| WO2003061699A1 (fr) * | 2001-12-27 | 2003-07-31 | Japan Tobacco, Inc. | Remedes pour affections allergiques |
| PT1501826E (pt) | 2002-02-01 | 2007-01-31 | Hoffmann La Roche | Idoles substituídos como agonistas de receptores alfa-1 |
| EP2130820A1 (en) | 2002-02-19 | 2009-12-09 | Shionogi & Co., Ltd. | Antipruritics |
| EP1487436A4 (en) | 2002-03-08 | 2009-06-03 | Signal Pharm Inc | POLYTHERAPY FOR TREATING, PREVENTING OR MANAGING PROLIFERATIVE DISORDERS AND CANCERS |
| AU2003214226A1 (en) * | 2002-03-18 | 2003-10-08 | Immugen Pharmaceuticals, Inc. | Topical formulations of resorcinols and cannibinoids and methods of use |
| FR2839718B1 (fr) | 2002-05-17 | 2004-06-25 | Sanofi Synthelabo | Derives d'indole, leur procede de preparation et les compositions pharmaceutiques en contenant |
| JP2005533809A (ja) | 2002-06-19 | 2005-11-10 | シェーリング コーポレイション | カンナビノイドレセプタアゴニスト |
| WO2004017922A2 (en) | 2002-08-23 | 2004-03-04 | University Of Connecticut | Keto cannabinoids with therapeutic indications |
| JP4455339B2 (ja) | 2002-11-25 | 2010-04-21 | シェーリング コーポレイション | カンナビノイドレセプターリガンド |
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| WO2005007111A2 (en) | 2003-07-11 | 2005-01-27 | Bristol-Myers Squibb Company | Tetrahydroquinoline derivatives as cannabinoid receptor modulators |
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| US7872033B2 (en) | 2007-04-17 | 2011-01-18 | Abbott Laboratories | Compounds as cannabinoid receptor ligands |
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| PL2606032T3 (pl) * | 2010-08-20 | 2015-07-31 | Univ Washington Through Its Center For Commercialization | Kompozycja i sposoby terapii glejakaep |
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| CN108794379A (zh) * | 2017-04-26 | 2018-11-13 | 华东师范大学 | 1h-吲哚-2-甲酰胺衍生物及其制备方法和应用 |
| AU2019210332A1 (en) | 2018-01-22 | 2020-09-10 | Pascal Biosciences Inc. | Cannabinoids and derivatives for promoting immunogenicity of tumor and infected cells |
| BR112022015379A2 (pt) | 2020-02-04 | 2022-09-27 | Mindset Pharma Inc | Derivados de 3-pirrolidino-indol como agentes psicodélicos serotonérgicos para o tratamento de distúrbios do snc |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RO77049A2 (ro) * | 1980-08-08 | 1981-06-22 | Institutul De Cercetari Chimico-Farmaceutice,Ro | Derivati de 2-metil-3-etilindol si procedeu de preparare a acestora |
| RO90049A2 (ro) * | 1984-12-25 | 1986-08-30 | Centrala Industriala De Medicamente Cosmetice,Coloranti Si Lacuri,Ro | Procedeu de preparare a clorhidratului hidrat de 1-(p-clorbenzoil)3-/2-(di-n-propilamino) etil/5-metoxi-2-metilindol |
| US5068234A (en) * | 1990-02-26 | 1991-11-26 | Sterling Drug Inc. | 3-arylcarbonyl-1-(c-attached-n-heteryl)-1h-indoles |
| US5081122A (en) * | 1990-03-05 | 1992-01-14 | Sterling Drug Inc. | Antiglaucoma compositions containing 4-arylcarbonyl-1-(4-morpholinyl)-lower-alkyl)-1H-indoles and method of use thereof |
| US5013837A (en) * | 1990-03-08 | 1991-05-07 | Sterling Drug Inc. | 3-Arylcarbonyl-1H-indole-containing compounds |
| US4973587A (en) * | 1990-03-08 | 1990-11-27 | Sterling Drug Inc. | 3-arylcarbonyl-1-aminoalkyl-1H-indole-containing antiglaucoma method |
| FR2735774B1 (fr) * | 1995-06-21 | 1997-09-12 | Sanofi Sa | Utilisation de composes agonistes du recepteur cb2 humain pour la preparation de medicaments immunomodulateurs, nouveaux composes agonistes du recepteur cb2 et les compositions pharmaceutiques les contenant |
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1995
- 1995-06-21 FR FR9507438A patent/FR2735774B1/fr not_active Expired - Fee Related
-
1996
- 1996-06-20 CA CA002225379A patent/CA2225379A1/en not_active Abandoned
- 1996-06-20 HU HU9900019A patent/HUP9900019A3/hu unknown
- 1996-06-20 WO PCT/FR1996/000959 patent/WO1997000860A1/fr active IP Right Grant
- 1996-06-20 BR BR9608640A patent/BR9608640A/pt not_active Application Discontinuation
- 1996-06-20 DE DE69616056T patent/DE69616056T2/de not_active Expired - Fee Related
- 1996-06-20 RU RU98101097/14A patent/RU2200736C2/ru not_active IP Right Cessation
- 1996-06-20 IL IL12263796A patent/IL122637A0/xx not_active IP Right Cessation
- 1996-06-20 NZ NZ312161A patent/NZ312161A/xx unknown
- 1996-06-20 TR TR97/01660T patent/TR199701660T1/xx unknown
- 1996-06-20 KR KR1019970709586A patent/KR19990028272A/ko active IP Right Grant
- 1996-06-20 JP JP50362997A patent/JP3417566B2/ja not_active Expired - Fee Related
- 1996-06-20 EP EP96922962A patent/EP0833818B1/fr not_active Expired - Lifetime
- 1996-06-20 PL PL96324185A patent/PL185598B1/pl not_active IP Right Cessation
- 1996-06-20 MX MX9710251A patent/MX9710251A/es not_active IP Right Cessation
- 1996-06-20 DK DK96922962T patent/DK0833818T3/da active
- 1996-06-20 UA UA97126177A patent/UA67717C2/uk unknown
- 1996-06-20 AU AU63632/96A patent/AU717858B2/en not_active Ceased
- 1996-06-20 SI SI9630401T patent/SI0833818T1/xx unknown
- 1996-06-20 EE EE9700345A patent/EE9700345A/et unknown
- 1996-06-20 CN CNB961961260A patent/CN1150166C/zh not_active Expired - Fee Related
- 1996-06-20 SK SK1735-97A patent/SK283660B6/sk unknown
- 1996-06-20 CZ CZ19974143A patent/CZ292630B6/cs not_active IP Right Cessation
- 1996-06-20 PT PT96922962T patent/PT833818E/pt unknown
- 1996-06-20 AT AT96922962T patent/ATE207054T1/de not_active IP Right Cessation
- 1996-06-20 ES ES96922962T patent/ES2165986T3/es not_active Expired - Lifetime
-
1997
- 1997-12-19 NO NO975989A patent/NO975989L/no not_active Application Discontinuation
- 1997-12-19 IS IS4637A patent/IS4637A/is unknown
- 1997-12-22 US US08/995,902 patent/US6013648A/en not_active Expired - Fee Related
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1998
- 1998-05-19 HK HK98104304A patent/HK1005093A1/xx not_active IP Right Cessation
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