SK372003A3 - Cyclic substituted aminomethyl compounds and medicaments containing said compounds - Google Patents
Cyclic substituted aminomethyl compounds and medicaments containing said compounds Download PDFInfo
- Publication number
- SK372003A3 SK372003A3 SK37-2003A SK372003A SK372003A3 SK 372003 A3 SK372003 A3 SK 372003A3 SK 372003 A SK372003 A SK 372003A SK 372003 A3 SK372003 A3 SK 372003A3
- Authority
- SK
- Slovakia
- Prior art keywords
- formula
- compounds
- alkyl
- pharmaceutically acceptable
- cycloalkyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 110
- 125000004122 cyclic group Chemical group 0.000 title claims abstract description 32
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 title claims abstract description 23
- 239000003814 drug Substances 0.000 title claims abstract description 19
- 238000000034 method Methods 0.000 claims abstract description 68
- 208000002193 Pain Diseases 0.000 claims abstract description 12
- 238000004519 manufacturing process Methods 0.000 claims abstract description 10
- 230000036407 pain Effects 0.000 claims abstract description 9
- 206010012735 Diarrhoea Diseases 0.000 claims abstract description 6
- 208000003251 Pruritus Diseases 0.000 claims abstract description 6
- 208000009205 Tinnitus Diseases 0.000 claims abstract description 6
- 231100000886 tinnitus Toxicity 0.000 claims abstract description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 5
- 150000003839 salts Chemical class 0.000 claims description 42
- -1 aminomethyl compound Chemical class 0.000 claims description 41
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 37
- 125000003118 aryl group Chemical group 0.000 claims description 30
- 239000000203 mixture Substances 0.000 claims description 29
- 125000000217 alkyl group Chemical group 0.000 claims description 28
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims description 21
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 20
- 125000000623 heterocyclic group Chemical group 0.000 claims description 20
- 229910052760 oxygen Inorganic materials 0.000 claims description 19
- 229910052717 sulfur Inorganic materials 0.000 claims description 19
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 18
- 150000003509 tertiary alcohols Chemical class 0.000 claims description 18
- 229960000583 acetic acid Drugs 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 13
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 12
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 10
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 claims description 9
- 229910000042 hydrogen bromide Inorganic materials 0.000 claims description 9
- 229930182817 methionine Natural products 0.000 claims description 9
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 8
- 150000003840 hydrochlorides Chemical class 0.000 claims description 8
- 239000012362 glacial acetic acid Substances 0.000 claims description 6
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 5
- 206010046543 Urinary incontinence Diseases 0.000 claims description 5
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
- 150000002576 ketones Chemical class 0.000 claims description 4
- 241000124008 Mammalia Species 0.000 claims description 3
- 239000003153 chemical reaction reagent Substances 0.000 claims description 3
- 230000007803 itching Effects 0.000 claims description 3
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims description 3
- 150000002902 organometallic compounds Chemical class 0.000 claims description 3
- 239000007800 oxidant agent Substances 0.000 claims description 3
- 229940124531 pharmaceutical excipient Drugs 0.000 claims description 3
- PSFSNTXSAWOKDQ-UHFFFAOYSA-N 1-[1-[(4-chlorophenyl)methyl]-3,4-dihydronaphthalen-2-yl]-n,n-dimethylmethanamine Chemical compound C12=CC=CC=C2CCC(CN(C)C)=C1CC1=CC=C(Cl)C=C1 PSFSNTXSAWOKDQ-UHFFFAOYSA-N 0.000 claims description 2
- PEQBIROCDNUXLB-CPNJWEJPSA-N 3-[(e)-[4-[(dimethylamino)methyl]-3,4-dihydro-2h-1-benzoxepin-5-ylidene]methyl]phenol Chemical compound CN(C)CC1CCOC2=CC=CC=C2\C1=C\C1=CC=CC(O)=C1 PEQBIROCDNUXLB-CPNJWEJPSA-N 0.000 claims description 2
- PEQBIROCDNUXLB-UYRXBGFRSA-N 3-[(z)-[4-[(dimethylamino)methyl]-3,4-dihydro-2h-1-benzoxepin-5-ylidene]methyl]phenol Chemical compound CN(C)CC1CCOC2=CC=CC=C2\C1=C/C1=CC=CC(O)=C1 PEQBIROCDNUXLB-UYRXBGFRSA-N 0.000 claims description 2
- WKUFHUPHTDMNHI-UHFFFAOYSA-N 3-[[2-[(dimethylamino)methyl]-3,4-dihydronaphthalen-1-yl]methyl]phenol Chemical compound C12=CC=CC=C2CCC(CN(C)C)=C1CC1=CC=CC(O)=C1 WKUFHUPHTDMNHI-UHFFFAOYSA-N 0.000 claims description 2
- YYMBOELYUQCEHB-UHFFFAOYSA-N 3-[[4-[(dimethylamino)methyl]-2,3-dihydro-1-benzoxepin-5-yl]methyl]phenol Chemical compound C12=CC=CC=C2OCCC(CN(C)C)=C1CC1=CC=CC(O)=C1 YYMBOELYUQCEHB-UHFFFAOYSA-N 0.000 claims description 2
- VARAKPPJHFCZGI-UHFFFAOYSA-N 5-[(4-chlorophenyl)methyl]-6-[(dimethylamino)methyl]-7,8-dihydronaphthalen-1-ol Chemical compound C12=CC=CC(O)=C2CCC(CN(C)C)=C1CC1=CC=C(Cl)C=C1 VARAKPPJHFCZGI-UHFFFAOYSA-N 0.000 claims description 2
- 239000000543 intermediate Substances 0.000 abstract description 3
- 206010021639 Incontinence Diseases 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
- 235000002639 sodium chloride Nutrition 0.000 description 30
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 26
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 25
- 239000000243 solution Substances 0.000 description 25
- 238000002844 melting Methods 0.000 description 20
- 230000008018 melting Effects 0.000 description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- 239000004743 Polypropylene Substances 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 12
- 230000000694 effects Effects 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
- 238000000926 separation method Methods 0.000 description 9
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 8
- 101100244562 Pseudomonas aeruginosa (strain ATCC 15692 / DSM 22644 / CIP 104116 / JCM 14847 / LMG 12228 / 1C / PRS 101 / PAO1) oprD gene Proteins 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
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 235000011054 acetic acid Nutrition 0.000 description 8
- 238000004440 column chromatography Methods 0.000 description 8
- 108700023159 delta Opioid Receptors Proteins 0.000 description 8
- 102000048124 delta Opioid Receptors Human genes 0.000 description 8
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
- 102000051367 mu Opioid Receptors Human genes 0.000 description 8
- 108020001612 μ-opioid receptors Proteins 0.000 description 8
- 238000000354 decomposition reaction Methods 0.000 description 7
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 7
- 229910052938 sodium sulfate Inorganic materials 0.000 description 7
- 235000011152 sodium sulphate Nutrition 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 6
- 239000003826 tablet Substances 0.000 description 6
- 239000005051 trimethylchlorosilane Substances 0.000 description 6
- 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 5
- 230000000202 analgesic effect Effects 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- 229940127240 opiate Drugs 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- RLQZIECDMISZHS-UHFFFAOYSA-N 2-phenylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C=CC(=O)C(C=2C=CC=CC=2)=C1 RLQZIECDMISZHS-UHFFFAOYSA-N 0.000 description 4
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 4
- 241000819038 Chichester Species 0.000 description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- IQDGSYLLQPDQDV-UHFFFAOYSA-N dimethylazanium;chloride Chemical compound Cl.CNC IQDGSYLLQPDQDV-UHFFFAOYSA-N 0.000 description 4
- 239000002552 dosage form Substances 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 229940013688 formic acid Drugs 0.000 description 4
- 235000019253 formic acid Nutrition 0.000 description 4
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- ZXRCAYWYTOIRQS-UHFFFAOYSA-N hydron;phenol;chloride Chemical compound Cl.OC1=CC=CC=C1 ZXRCAYWYTOIRQS-UHFFFAOYSA-N 0.000 description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 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
- 239000003960 organic solvent Substances 0.000 description 4
- 238000006467 substitution reaction Methods 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 238000010626 work up procedure Methods 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- 208000000094 Chronic Pain Diseases 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
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 230000003502 anti-nociceptive effect Effects 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 3
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 230000001684 chronic effect Effects 0.000 description 3
- 235000015165 citric acid Nutrition 0.000 description 3
- 229960004106 citric acid Drugs 0.000 description 3
- 238000013016 damping Methods 0.000 description 3
- XHFGWHUWQXTGAT-UHFFFAOYSA-N dimethylamine hydrochloride Natural products CNC(C)C XHFGWHUWQXTGAT-UHFFFAOYSA-N 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 238000001727 in vivo Methods 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 3
- 229960005181 morphine Drugs 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 150000007524 organic acids Chemical class 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 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
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 2
- KAFZOLYKKCWUBI-HPMAGDRPSA-N (2s)-2-[[(2s)-2-[[(2s)-1-[(2s)-3-amino-2-[[(2s)-2-[[(2s)-2-(3-cyclohexylpropanoylamino)-4-methylpentanoyl]amino]-5-methylhexanoyl]amino]propanoyl]pyrrolidine-2-carbonyl]amino]-5-(diaminomethylideneamino)pentanoyl]amino]butanediamide Chemical compound N([C@@H](CC(C)C)C(=O)N[C@@H](CCC(C)C)C(=O)N[C@@H](CN)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCN=C(N)N)C(=O)N[C@@H](CC(N)=O)C(N)=O)C(=O)CCC1CCCCC1 KAFZOLYKKCWUBI-HPMAGDRPSA-N 0.000 description 2
- AQTXTCPSTSPQIL-OKOHOLKASA-N 1-[(5z)-5-[(4-chlorophenyl)methylidene]-3,4-dihydro-2h-1-benzoxepin-4-yl]-n,n-dimethylmethanamine;hydrochloride Chemical compound Cl.CN(C)CC1CCOC2=CC=CC=C2\C1=C/C1=CC=C(Cl)C=C1 AQTXTCPSTSPQIL-OKOHOLKASA-N 0.000 description 2
- LJUVKXQQVMEKJD-UHFFFAOYSA-N 1-[1-[(2-methoxyphenyl)methyl]-3,4-dihydronaphthalen-2-yl]-n,n-dimethylmethanamine;hydrochloride Chemical compound Cl.COC1=CC=CC=C1CC1=C(CN(C)C)CCC2=CC=CC=C12 LJUVKXQQVMEKJD-UHFFFAOYSA-N 0.000 description 2
- GQJKCEREGLSIRS-UHFFFAOYSA-N 1-[1-[(3-methoxyphenyl)methyl]-3,4-dihydronaphthalen-2-yl]-n,n-dimethylmethanamine;hydrochloride Chemical compound Cl.COC1=CC=CC(CC=2C3=CC=CC=C3CCC=2CN(C)C)=C1 GQJKCEREGLSIRS-UHFFFAOYSA-N 0.000 description 2
- OMCOACHXKJOZMD-UHFFFAOYSA-N 2-[(dimethylamino)methyl]-3,4-dihydro-2h-naphthalen-1-one Chemical compound C1=CC=C2C(=O)C(CN(C)C)CCC2=C1 OMCOACHXKJOZMD-UHFFFAOYSA-N 0.000 description 2
- WQKRFIXDLINYDJ-XTWSRORZSA-N 3-[(e)-[4-[(dimethylamino)methyl]-3,4-dihydro-2h-1-benzoxepin-5-ylidene]methyl]phenol;hydrochloride Chemical compound Cl.CN(C)CC1CCOC2=CC=CC=C2\C1=C\C1=CC=CC(O)=C1 WQKRFIXDLINYDJ-XTWSRORZSA-N 0.000 description 2
- WQKRFIXDLINYDJ-OKOHOLKASA-N 3-[(z)-[4-[(dimethylamino)methyl]-3,4-dihydro-2h-1-benzoxepin-5-ylidene]methyl]phenol;hydrochloride Chemical compound Cl.CN(C)CC1CCOC2=CC=CC=C2\C1=C/C1=CC=CC(O)=C1 WQKRFIXDLINYDJ-OKOHOLKASA-N 0.000 description 2
- 125000006497 3-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 description 2
- VEAHGDVZOWZJQW-UHFFFAOYSA-N 4-[(dimethylamino)methyl]-5-[(3-methoxyphenyl)methyl]-3,4-dihydro-2h-1-benzoxepin-5-ol Chemical compound COC1=CC=CC(CC2(O)C3=CC=CC=C3OCCC2CN(C)C)=C1 VEAHGDVZOWZJQW-UHFFFAOYSA-N 0.000 description 2
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 2
- RREANTFLPGEWEN-MBLPBCRHSA-N 7-[4-[[(3z)-3-[4-amino-5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidin-2-yl]imino-5-fluoro-2-oxoindol-1-yl]methyl]piperazin-1-yl]-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(\N=C/3C4=CC(F)=CC=C4N(CN4CCN(CC4)C=4C(=CC=5C(=O)C(C(O)=O)=CN(C=5C=4)C4CC4)F)C\3=O)=NC=2)N)=C1 RREANTFLPGEWEN-MBLPBCRHSA-N 0.000 description 2
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- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
- 229910000368 zinc sulfate Inorganic materials 0.000 description 1
- 229960001763 zinc sulfate Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
- C07D335/04—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D335/06—Benzothiopyrans; Hydrogenated benzothiopyrans
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/12—Antidiarrhoeals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/06—Anti-spasmodics
-
- 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
- A61P17/00—Drugs for dermatological disorders
- A61P17/04—Antipruritics
-
- 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
-
- 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
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- 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
- A61P25/20—Hypnotics; Sedatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/16—Otologicals
-
- 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]
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/26—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring
- C07C211/29—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/46—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C215/64—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with rings other than six-membered aromatic rings being part of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/54—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C217/74—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with rings other than six-membered aromatic rings being part of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D313/00—Heterocyclic compounds containing rings of more than six members having one oxygen atom as the only ring hetero atom
- C07D313/02—Seven-membered rings
- C07D313/06—Seven-membered rings condensed with carbocyclic rings or ring systems
- C07D313/08—Seven-membered rings condensed with carbocyclic rings or ring systems condensed with one six-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D337/00—Heterocyclic compounds containing rings of more than six members having one sulfur atom as the only ring hetero atom
- C07D337/02—Seven-membered rings
- C07D337/06—Seven-membered rings condensed with carbocyclic rings or ring systems
- C07D337/08—Seven-membered rings condensed with carbocyclic rings or ring systems condensed with one six-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/12—One of the condensed rings being a six-membered aromatic ring the other ring being at least seven-membered
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Urology & Nephrology (AREA)
- Dermatology (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Anesthesiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyrane Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10033459A DE10033459A1 (de) | 2000-07-10 | 2000-07-10 | Cyclische substituierte Aminomethylverbindungen und diese Verbindungen enthaltende Arzeimittel |
| PCT/EP2001/007750 WO2002008218A1 (de) | 2000-07-10 | 2001-07-06 | Cyclische substituierte aminomethylverbindungen und diese verbindungen enthaltende arzneimittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK372003A3 true SK372003A3 (en) | 2003-06-03 |
Family
ID=7648406
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK37-2003A SK372003A3 (en) | 2000-07-10 | 2001-07-06 | Cyclic substituted aminomethyl compounds and medicaments containing said compounds |
Country Status (28)
| Country | Link |
|---|---|
| US (1) | US6890952B2 (es) |
| EP (1) | EP1299373B1 (es) |
| JP (1) | JP2004504394A (es) |
| KR (1) | KR100821113B1 (es) |
| CN (1) | CN1179958C (es) |
| AR (1) | AR032464A1 (es) |
| AT (1) | ATE286891T1 (es) |
| AU (2) | AU6912401A (es) |
| BR (1) | BR0112447A (es) |
| CA (1) | CA2415196A1 (es) |
| CZ (1) | CZ301135B6 (es) |
| DE (2) | DE10033459A1 (es) |
| EC (1) | ECSP034416A (es) |
| ES (1) | ES2234851T3 (es) |
| HK (1) | HK1054932A1 (es) |
| HU (1) | HUP0302817A3 (es) |
| IL (2) | IL153825A0 (es) |
| MX (1) | MXPA02012925A (es) |
| MY (1) | MY134060A (es) |
| NO (1) | NO20030105L (es) |
| NZ (1) | NZ523089A (es) |
| PE (1) | PE20020255A1 (es) |
| PL (1) | PL204123B1 (es) |
| PT (1) | PT1299373E (es) |
| RU (1) | RU2003102610A (es) |
| SK (1) | SK372003A3 (es) |
| WO (1) | WO2002008218A1 (es) |
| ZA (1) | ZA200301048B (es) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102004034619A1 (de) | 2004-07-16 | 2006-02-23 | Grünenthal GmbH | Substituierte Aminoverbindungen als 5-HT/NA Uptakehemmer |
| EP1893568A2 (en) * | 2005-06-07 | 2008-03-05 | Neurocrine Biosciences, Inc. | Monoamine re-uptake inhibitors and methods relating thereto |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE922703C (de) | 1951-02-03 | 1955-01-24 | Hans Kenner | Stanzvorlage zum Ausstanzen von Reissverschlusskrampen und Verfahren sowie Vorrichtung zum Herstellen derselben |
| CH394229A (de) * | 1958-03-20 | 1965-06-30 | Ciba Geigy | Verfahren zur Herstellung von 3-Aralkyl-2-tert.-aminoalkyl-indenen |
| US3072716A (en) * | 1959-03-18 | 1963-01-08 | Ciba Geigy Corp | Substituted indenes |
| US3142682A (en) * | 1961-11-21 | 1964-07-28 | Ciba Geigy Corp | Tertiary amino derivatives of chromans and homo-chromans |
| US3956391A (en) * | 1973-06-04 | 1976-05-11 | Sandoz, Inc. | Amino substituted tetrahydropleiadenes |
| JPS61130287A (ja) * | 1984-11-30 | 1986-06-18 | Suntory Ltd | １−ベンズオキセピン誘導体 |
| DE19805370A1 (de) * | 1997-03-14 | 1998-09-17 | Gruenenthal Gmbh | Substituierte Aminoverbindungen und ihre Verwendung als analgetisch wirksame Substanzen |
| DE19755480A1 (de) * | 1997-12-13 | 1999-06-24 | Gruenenthal Gmbh | Substituierte heterocyclische Benzocycloalkene und ihre Verwendung als analgetisch wirksame Substanzen |
-
2000
- 2000-07-10 DE DE10033459A patent/DE10033459A1/de not_active Withdrawn
-
2001
- 2001-07-05 MY MYPI20013200 patent/MY134060A/en unknown
- 2001-07-06 NZ NZ523089A patent/NZ523089A/en unknown
- 2001-07-06 BR BR0112447-1A patent/BR0112447A/pt not_active IP Right Cessation
- 2001-07-06 SK SK37-2003A patent/SK372003A3/sk unknown
- 2001-07-06 WO PCT/EP2001/007750 patent/WO2002008218A1/de active IP Right Grant
- 2001-07-06 RU RU2003102610/04A patent/RU2003102610A/ru not_active Application Discontinuation
- 2001-07-06 ES ES01947447T patent/ES2234851T3/es not_active Expired - Lifetime
- 2001-07-06 AU AU6912401A patent/AU6912401A/xx active Pending
- 2001-07-06 AR ARP010103240A patent/AR032464A1/es unknown
- 2001-07-06 AU AU2001269124A patent/AU2001269124B2/en not_active Ceased
- 2001-07-06 JP JP2002514124A patent/JP2004504394A/ja active Pending
- 2001-07-06 PT PT01947447T patent/PT1299373E/pt unknown
- 2001-07-06 CZ CZ20030088A patent/CZ301135B6/cs not_active IP Right Cessation
- 2001-07-06 HU HU0302817A patent/HUP0302817A3/hu unknown
- 2001-07-06 KR KR1020037000317A patent/KR100821113B1/ko not_active IP Right Cessation
- 2001-07-06 MX MXPA02012925A patent/MXPA02012925A/es active IP Right Grant
- 2001-07-06 DE DE50105073T patent/DE50105073D1/de not_active Expired - Lifetime
- 2001-07-06 AT AT01947447T patent/ATE286891T1/de active
- 2001-07-06 EP EP01947447A patent/EP1299373B1/de not_active Expired - Lifetime
- 2001-07-06 CN CNB018125557A patent/CN1179958C/zh not_active Expired - Fee Related
- 2001-07-06 IL IL15382501A patent/IL153825A0/xx active IP Right Grant
- 2001-07-06 PL PL360389A patent/PL204123B1/pl not_active IP Right Cessation
- 2001-07-06 CA CA002415196A patent/CA2415196A1/en not_active Abandoned
- 2001-07-09 PE PE2001000678A patent/PE20020255A1/es not_active Application Discontinuation
-
2003
- 2003-01-06 EC EC2003004416A patent/ECSP034416A/es unknown
- 2003-01-07 IL IL153825A patent/IL153825A/en not_active IP Right Cessation
- 2003-01-09 NO NO20030105A patent/NO20030105L/no not_active Application Discontinuation
- 2003-01-10 US US10/339,671 patent/US6890952B2/en not_active Expired - Fee Related
- 2003-02-06 ZA ZA200301048A patent/ZA200301048B/en unknown
- 2003-10-06 HK HK03107164A patent/HK1054932A1/xx not_active IP Right Cessation
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FB9A | Suspension of patent application procedure |