DE2912026C2 - - Google Patents
Info
- Publication number
- DE2912026C2 DE2912026C2 DE2912026A DE2912026A DE2912026C2 DE 2912026 C2 DE2912026 C2 DE 2912026C2 DE 2912026 A DE2912026 A DE 2912026A DE 2912026 A DE2912026 A DE 2912026A DE 2912026 C2 DE2912026 C2 DE 2912026C2
- Authority
- DE
- Germany
- Prior art keywords
- acid addition
- methyl
- piperidine
- addition salts
- toxic acid
- 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.)
- Expired - Lifetime
Links
- 150000001875 compounds Chemical class 0.000 claims description 52
- 239000002253 acid Substances 0.000 claims description 44
- 238000007792 addition Methods 0.000 claims description 36
- 150000003839 salts Chemical class 0.000 claims description 35
- 231100000252 nontoxic Toxicity 0.000 claims description 25
- 230000003000 nontoxic effect Effects 0.000 claims description 25
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 14
- 125000005843 halogen group Chemical group 0.000 claims description 12
- 238000010992 reflux Methods 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- JXPCRJDMUSNASY-UHFFFAOYSA-N 1-(4-benzhydrylpiperidin-1-yl)-n-octylmethanimine Chemical compound C1CN(C=NCCCCCCCC)CCC1C(C=1C=CC=CC=1)C1=CC=CC=C1 JXPCRJDMUSNASY-UHFFFAOYSA-N 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 7
- HPYKRLQBMUPOFA-UHFFFAOYSA-N piperidin-1-ylmethanimine Chemical class N=CN1CCCCC1 HPYKRLQBMUPOFA-UHFFFAOYSA-N 0.000 claims description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 229920006395 saturated elastomer Polymers 0.000 claims description 6
- 239000004215 Carbon black (E152) Substances 0.000 claims description 5
- 229930195733 hydrocarbon Natural products 0.000 claims description 5
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- XBTWVFUQSUPGLB-UHFFFAOYSA-N 4-[[1-(octyliminomethyl)piperidin-4-yl]-phenylmethyl]phenol Chemical compound C1CN(C=NCCCCCCCC)CCC1C(C=1C=CC(O)=CC=1)C1=CC=CC=C1 XBTWVFUQSUPGLB-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
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 4
- 230000027119 gastric acid secretion Effects 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 4
- UJGBYIZKUOICBM-UHFFFAOYSA-N (3-benzhydrylpiperidin-1-yl)methanimine Chemical compound C1N(C=N)CCCC1C(C=1C=CC=CC=1)C1=CC=CC=C1 UJGBYIZKUOICBM-UHFFFAOYSA-N 0.000 claims description 3
- NBZJVTDQNQQIBS-UHFFFAOYSA-N 1-(1-methanimidoyl-4-phenylpiperidin-4-yl)ethanone Chemical compound C=1C=CC=CC=1C1(C(=O)C)CCN(C=N)CC1 NBZJVTDQNQQIBS-UHFFFAOYSA-N 0.000 claims description 3
- DHLFRMXOIRBEJT-UHFFFAOYSA-N 1-(3-benzhydrylpiperidin-1-yl)-n-octylmethanimine Chemical compound C1N(C=NCCCCCCCC)CCCC1C(C=1C=CC=CC=1)C1=CC=CC=C1 DHLFRMXOIRBEJT-UHFFFAOYSA-N 0.000 claims description 3
- QUQDKIUDCJNDDP-UHFFFAOYSA-N 1-[4-(9h-fluoren-9-yl)piperidin-1-yl]-n-octylmethanimine Chemical compound C1CN(C=NCCCCCCCC)CCC1C1C2=CC=CC=C2C2=CC=CC=C21 QUQDKIUDCJNDDP-UHFFFAOYSA-N 0.000 claims description 3
- 229910021607 Silver chloride Inorganic materials 0.000 claims description 3
- PAAFNOAYYZCGRK-UHFFFAOYSA-N [1-(octyliminomethyl)piperidin-4-yl]-diphenylmethanol Chemical compound C1CN(C=NCCCCCCCC)CCC1C(O)(C=1C=CC=CC=1)C1=CC=CC=C1 PAAFNOAYYZCGRK-UHFFFAOYSA-N 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 claims description 3
- WKOWVPWMBLXPNA-UHFFFAOYSA-N (4-benzhydrylpiperidin-1-yl)methanimine Chemical compound C1CN(C=N)CCC1C(C=1C=CC=CC=1)C1=CC=CC=C1 WKOWVPWMBLXPNA-UHFFFAOYSA-N 0.000 claims description 2
- CEBSSFHQBJQQFS-UHFFFAOYSA-N 1-(4-benzhydrylpiperidin-1-yl)-n-(2-phenylethyl)methanimine Chemical compound C1CC(C(C=2C=CC=CC=2)C=2C=CC=CC=2)CCN1C=NCCC1=CC=CC=C1 CEBSSFHQBJQQFS-UHFFFAOYSA-N 0.000 claims description 2
- MGJDROYKVQVIDO-UHFFFAOYSA-N 1-(4-benzhydrylpiperidin-1-yl)-n-[(4-chlorophenyl)methyl]methanimine Chemical compound C1=CC(Cl)=CC=C1CN=CN1CCC(C(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 MGJDROYKVQVIDO-UHFFFAOYSA-N 0.000 claims description 2
- DTNFAMFITREREA-UHFFFAOYSA-N 1-(4-benzhydrylpiperidin-1-yl)-n-benzylmethanimine Chemical compound C=1C=CC=CC=1CN=CN(CC1)CCC1C(C=1C=CC=CC=1)C1=CC=CC=C1 DTNFAMFITREREA-UHFFFAOYSA-N 0.000 claims description 2
- YOEZYELQYRDDQW-UHFFFAOYSA-N 1-(4-benzhydrylpiperidin-1-yl)-n-butylmethanimine Chemical compound C1CN(C=NCCCC)CCC1C(C=1C=CC=CC=1)C1=CC=CC=C1 YOEZYELQYRDDQW-UHFFFAOYSA-N 0.000 claims description 2
- XGQIAOFTXDPNPU-UHFFFAOYSA-N 1-(4-benzhydrylpiperidin-1-yl)-n-decylmethanimine Chemical compound C1CN(C=NCCCCCCCCCC)CCC1C(C=1C=CC=CC=1)C1=CC=CC=C1 XGQIAOFTXDPNPU-UHFFFAOYSA-N 0.000 claims description 2
- OBNAPUIVNAHAPU-UHFFFAOYSA-N 1-(4-benzhydrylpiperidin-1-yl)-n-ethylmethanimine Chemical compound C1CN(C=NCC)CCC1C(C=1C=CC=CC=1)C1=CC=CC=C1 OBNAPUIVNAHAPU-UHFFFAOYSA-N 0.000 claims description 2
- DWTVABJWHCKNQE-UHFFFAOYSA-N 1-(4-benzhydrylpiperidin-1-yl)-n-octylethanimine Chemical compound C1CN(C(C)=NCCCCCCCC)CCC1C(C=1C=CC=CC=1)C1=CC=CC=C1 DWTVABJWHCKNQE-UHFFFAOYSA-N 0.000 claims description 2
- XCYGHYMVPSURQN-UHFFFAOYSA-N 1-(4-benzhydrylpiperidin-1-yl)-n-propan-2-ylmethanimine Chemical compound C1CN(C=NC(C)C)CCC1C(C=1C=CC=CC=1)C1=CC=CC=C1 XCYGHYMVPSURQN-UHFFFAOYSA-N 0.000 claims description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 150000004820 halides Chemical group 0.000 claims description 2
- 239000003112 inhibitor Substances 0.000 claims description 2
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 2
- HVBBBNNOVORYPZ-UHFFFAOYSA-N 1-(4-benzhydrylpiperidin-1-yl)-n-(4-phenylbutyl)methanimine Chemical compound C1CC(C(C=2C=CC=CC=2)C=2C=CC=CC=2)CCN1C=NCCCCC1=CC=CC=C1 HVBBBNNOVORYPZ-UHFFFAOYSA-N 0.000 claims 1
- DROSUKHUMWESGP-UHFFFAOYSA-N 1-(4-benzhydrylpiperidin-1-yl)-n-prop-2-ynylmethanimine Chemical compound C1CN(C=NCC#C)CCC1C(C=1C=CC=CC=1)C1=CC=CC=C1 DROSUKHUMWESGP-UHFFFAOYSA-N 0.000 claims 1
- -1 alkyl radical Chemical class 0.000 description 42
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 33
- 239000000243 solution Substances 0.000 description 30
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 239000000047 product Substances 0.000 description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 18
- 239000000203 mixture Substances 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- 239000007858 starting material Substances 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 13
- 239000003921 oil Substances 0.000 description 13
- 239000007787 solid Substances 0.000 description 13
- IHQJXDLHKZENCY-UHFFFAOYSA-N 4-benzhydrylpiperidine-1-carbaldehyde Chemical compound C1CN(C=O)CCC1C(C=1C=CC=CC=1)C1=CC=CC=C1 IHQJXDLHKZENCY-UHFFFAOYSA-N 0.000 description 12
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 10
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 10
- LUYLEMZRJQTGPM-UHFFFAOYSA-N 4-benzhydrylpiperidine Chemical compound C1CNCCC1C(C=1C=CC=CC=1)C1=CC=CC=C1 LUYLEMZRJQTGPM-UHFFFAOYSA-N 0.000 description 9
- 241000700159 Rattus Species 0.000 description 9
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- SDSVJQZSTMOVFF-UHFFFAOYSA-N 4-benzhydrylpiperidine-1-carbothialdehyde Chemical compound C1CN(C=S)CCC1C(C=1C=CC=CC=1)C1=CC=CC=C1 SDSVJQZSTMOVFF-UHFFFAOYSA-N 0.000 description 7
- 210000002784 stomach Anatomy 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- 229960000583 acetic acid Drugs 0.000 description 5
- 150000001408 amides Chemical class 0.000 description 5
- 239000000969 carrier Substances 0.000 description 5
- 239000012458 free base Substances 0.000 description 5
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- JPUTTYRVDANTBN-UHFFFAOYSA-N ethyl methanimidate;hydrochloride Chemical compound Cl.CCOC=N JPUTTYRVDANTBN-UHFFFAOYSA-N 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 239000001530 fumaric acid Substances 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- 150000003053 piperidines Chemical class 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 239000003826 tablet Substances 0.000 description 4
- KRTMQDOLKIGPAH-WLHGVMLRSA-N 1-(4-benzhydrylpiperidin-1-yl)-n-octylmethanimine;(e)-but-2-enedioic acid Chemical compound OC(=O)\C=C\C(O)=O.C1CN(C=NCCCCCCCC)CCC1C(C=1C=CC=CC=1)C1=CC=CC=C1 KRTMQDOLKIGPAH-WLHGVMLRSA-N 0.000 description 3
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000003213 activating effect Effects 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 150000008282 halocarbons Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- AGNFWIZBEATIAK-UHFFFAOYSA-N 4-phenylbutylamine Chemical compound NCCCCC1=CC=CC=C1 AGNFWIZBEATIAK-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 244000061176 Nicotiana tabacum Species 0.000 description 2
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 2
- BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000007868 Raney catalyst Substances 0.000 description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 2
- 210000004051 gastric juice Anatomy 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- 229940071870 hydroiodic acid Drugs 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- 239000006186 oral dosage form Substances 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 229910003446 platinum oxide Inorganic materials 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- 230000028327 secretion Effects 0.000 description 2
- 239000013049 sediment Substances 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 2
- 238000011477 surgical intervention Methods 0.000 description 2
- 238000001356 surgical procedure Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- SFRBZQLZBAPXPZ-UHFFFAOYSA-N (4-benzhydrylpiperidin-1-yl)methanimine;hydrate;hydrochloride Chemical compound O.Cl.C1CN(C=N)CCC1C(C=1C=CC=CC=1)C1=CC=CC=C1 SFRBZQLZBAPXPZ-UHFFFAOYSA-N 0.000 description 1
- YMVFJGSXZNNUDW-UHFFFAOYSA-N (4-chlorophenyl)methanamine Chemical compound NCC1=CC=C(Cl)C=C1 YMVFJGSXZNNUDW-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- ZOVXMZUMTUSQTA-UHFFFAOYSA-N 1-(4-benzhydrylidenepiperidin-1-yl)-n-octylmethanimine Chemical compound C1CN(C=NCCCCCCCC)CCC1=C(C=1C=CC=CC=1)C1=CC=CC=C1 ZOVXMZUMTUSQTA-UHFFFAOYSA-N 0.000 description 1
- VPAFQIBPKJHWPX-UHFFFAOYSA-N 1-(4-benzhydrylpiperidin-1-yl)-N-ethylmethanimine oxalic acid Chemical compound C(C(=O)O)(=O)O.C1(=CC=CC=C1)C(C1CCN(CC1)C=NCC)C1=CC=CC=C1 VPAFQIBPKJHWPX-UHFFFAOYSA-N 0.000 description 1
- MXBDXXYGMKLQJM-WLHGVMLRSA-N 1-(4-benzhydrylpiperidin-1-yl)-n-dodecylmethanimine;(e)-but-2-enedioic acid Chemical compound OC(=O)\C=C\C(O)=O.C1CN(C=NCCCCCCCCCCCC)CCC1C(C=1C=CC=CC=1)C1=CC=CC=C1 MXBDXXYGMKLQJM-WLHGVMLRSA-N 0.000 description 1
- RRQHGUAGZHTIQO-UHFFFAOYSA-N 1-(4-benzhydrylpiperidin-1-yl)-n-hexylmethanimine Chemical compound C1CN(C=NCCCCCC)CCC1C(C=1C=CC=CC=1)C1=CC=CC=C1 RRQHGUAGZHTIQO-UHFFFAOYSA-N 0.000 description 1
- LSAGFMSUHAFCOI-JITBQSAISA-N 1-(4-benzhydrylpiperidin-1-yl)-n-octylmethanimine;(e)-but-2-enedioic acid;hydrate Chemical compound O.OC(=O)\C=C\C(O)=O.C1CN(C=NCCCCCCCC)CCC1C(C=1C=CC=CC=1)C1=CC=CC=C1 LSAGFMSUHAFCOI-JITBQSAISA-N 0.000 description 1
- IQAXPGYCYWUFEL-UHFFFAOYSA-N 1-[4-[(4-methoxyphenyl)-phenylmethyl]piperidin-1-yl]-n-octylmethanimine Chemical compound C1CN(C=NCCCCCCCC)CCC1C(C=1C=CC(OC)=CC=1)C1=CC=CC=C1 IQAXPGYCYWUFEL-UHFFFAOYSA-N 0.000 description 1
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- 125000005485 noradamantyl group Chemical group 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- GEVPUGOOGXGPIO-UHFFFAOYSA-N oxalic acid;dihydrate Chemical compound O.O.OC(=O)C(O)=O GEVPUGOOGXGPIO-UHFFFAOYSA-N 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 229940117803 phenethylamine Drugs 0.000 description 1
- SKFLCXNDKRUHTA-UHFFFAOYSA-N phenyl(pyridin-4-yl)methanone Chemical compound C=1C=NC=CC=1C(=O)C1=CC=CC=C1 SKFLCXNDKRUHTA-UHFFFAOYSA-N 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
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- JKANAVGODYYCQF-UHFFFAOYSA-N prop-2-yn-1-amine Chemical compound NCC#C JKANAVGODYYCQF-UHFFFAOYSA-N 0.000 description 1
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- 239000012264 purified product Substances 0.000 description 1
- JZWFDVDETGFGFC-UHFFFAOYSA-N salacetamide Chemical group CC(=O)NC(=O)C1=CC=CC=C1O JZWFDVDETGFGFC-UHFFFAOYSA-N 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/16—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing only one pyridine ring
-
- 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
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- 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
- C07D211/08—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/10—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
- C07D211/12—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms with only hydrogen atoms attached to the ring nitrogen atom
-
- 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
- C07D211/08—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/10—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
- C07D211/16—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms with acylated ring nitrogen atom
-
- 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
- C07D211/08—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
-
- 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
- C07D211/08—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/20—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
- C07D211/22—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms
-
- 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
- C07D211/08—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/30—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom
- C07D211/32—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom by oxygen atoms
-
- 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
- C07D211/70—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/30—Oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US89141978A | 1978-03-29 | 1978-03-29 | |
US1020979A | 1979-02-08 | 1979-02-08 |
Publications (2)
Publication Number | Publication Date |
---|---|
DE2912026A1 DE2912026A1 (de) | 1979-10-11 |
DE2912026C2 true DE2912026C2 (en, 2012) | 1990-04-05 |
Family
ID=26680913
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE19792912026 Granted DE2912026A1 (de) | 1978-03-29 | 1979-03-27 | Substituierte n-iminomethylpiperidine, verfahren zu deren herstellung und diese verbindungen enthaltende arzneimittel |
Country Status (24)
Country | Link |
---|---|
JP (1) | JPS54132580A (en, 2012) |
AT (1) | AT372081B (en, 2012) |
AU (1) | AU523867B2 (en, 2012) |
CA (1) | CA1140118A (en, 2012) |
CH (1) | CH639071A5 (en, 2012) |
DE (1) | DE2912026A1 (en, 2012) |
DK (1) | DK124979A (en, 2012) |
ES (1) | ES479033A1 (en, 2012) |
FI (1) | FI791035A7 (en, 2012) |
FR (1) | FR2421169A1 (en, 2012) |
GB (1) | GB2017689B (en, 2012) |
GR (1) | GR65192B (en, 2012) |
IE (1) | IE47898B1 (en, 2012) |
IL (1) | IL56962A (en, 2012) |
IT (1) | IT1116525B (en, 2012) |
NL (1) | NL7902465A (en, 2012) |
NO (1) | NO791026L (en, 2012) |
NZ (1) | NZ189977A (en, 2012) |
PH (1) | PH15760A (en, 2012) |
PT (1) | PT69383A (en, 2012) |
SE (1) | SE7902724L (en, 2012) |
SU (1) | SU1158042A3 (en, 2012) |
YU (1) | YU73179A (en, 2012) |
ZW (1) | ZW6479A1 (en, 2012) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5889006A (en) * | 1995-02-23 | 1999-03-30 | Schering Corporation | Muscarinic antagonists |
IL117149A0 (en) * | 1995-02-23 | 1996-06-18 | Schering Corp | Muscarinic antagonists |
SE508513C2 (sv) * | 1997-02-14 | 1998-10-12 | Ericsson Telefon Ab L M | Mikrostripantenn samt gruppantenn |
TWI245763B (en) * | 1998-04-02 | 2005-12-21 | Janssen Pharmaceutica Nv | Biocidal benzylbiphenyl derivatives |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CH563109A5 (en, 2012) * | 1972-03-17 | 1975-06-30 | Ciba Geigy Ag |
-
1979
- 1979-03-19 AU AU45322/79A patent/AU523867B2/en not_active Ceased
- 1979-03-20 GB GB7909671A patent/GB2017689B/en not_active Expired
- 1979-03-22 PT PT69383A patent/PT69383A/pt unknown
- 1979-03-23 NZ NZ189977A patent/NZ189977A/en unknown
- 1979-03-27 JP JP3516879A patent/JPS54132580A/ja active Granted
- 1979-03-27 SE SE7902724A patent/SE7902724L/xx not_active Application Discontinuation
- 1979-03-27 DE DE19792912026 patent/DE2912026A1/de active Granted
- 1979-03-27 YU YU00731/79A patent/YU73179A/xx unknown
- 1979-03-27 DK DK124979A patent/DK124979A/da not_active Application Discontinuation
- 1979-03-28 IT IT48515/79A patent/IT1116525B/it active
- 1979-03-28 SU SU792745899A patent/SU1158042A3/ru active
- 1979-03-28 IL IL56962A patent/IL56962A/xx unknown
- 1979-03-28 FI FI791035A patent/FI791035A7/fi not_active Application Discontinuation
- 1979-03-28 ZW ZW64/79A patent/ZW6479A1/xx unknown
- 1979-03-28 AT AT0230979A patent/AT372081B/de not_active IP Right Cessation
- 1979-03-28 PH PH22331A patent/PH15760A/en unknown
- 1979-03-28 ES ES479033A patent/ES479033A1/es not_active Expired
- 1979-03-28 CA CA000324324A patent/CA1140118A/en not_active Expired
- 1979-03-28 NO NO791026A patent/NO791026L/no unknown
- 1979-03-29 CH CH292779A patent/CH639071A5/de not_active IP Right Cessation
- 1979-03-29 NL NL7902465A patent/NL7902465A/xx not_active Application Discontinuation
- 1979-03-29 FR FR7907919A patent/FR2421169A1/fr active Granted
- 1979-03-29 GR GR58719A patent/GR65192B/el unknown
- 1979-08-08 IE IE650/79A patent/IE47898B1/en unknown
Also Published As
Publication number | Publication date |
---|---|
IL56962A (en) | 1983-03-31 |
CA1140118A (en) | 1983-01-25 |
GB2017689A (en) | 1979-10-10 |
AT372081B (de) | 1983-08-25 |
FR2421169A1 (fr) | 1979-10-26 |
YU73179A (en) | 1983-12-31 |
IT7948515A0 (it) | 1979-03-28 |
DK124979A (da) | 1979-09-30 |
CH639071A5 (de) | 1983-10-31 |
IE790650L (en) | 1979-09-29 |
NO791026L (no) | 1979-10-02 |
AU4532279A (en) | 1979-10-04 |
GB2017689B (en) | 1982-09-02 |
IT1116525B (it) | 1986-02-10 |
ZW6479A1 (en) | 1980-11-26 |
JPS54132580A (en) | 1979-10-15 |
DE2912026A1 (de) | 1979-10-11 |
NL7902465A (nl) | 1979-10-02 |
IE47898B1 (en) | 1984-07-11 |
IL56962A0 (en) | 1979-05-31 |
SE7902724L (sv) | 1979-09-30 |
PT69383A (en) | 1979-04-01 |
ES479033A1 (es) | 1980-06-16 |
JPS6217588B2 (en, 2012) | 1987-04-18 |
FR2421169B1 (en, 2012) | 1983-05-27 |
FI791035A7 (fi) | 1981-01-01 |
AU523867B2 (en) | 1982-08-19 |
NZ189977A (en) | 1984-05-31 |
SU1158042A3 (ru) | 1985-05-23 |
GR65192B (en) | 1980-07-29 |
ATA230979A (de) | 1983-01-15 |
PH15760A (en) | 1983-03-22 |
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Representative=s name: VOSSIUS, V., DIPL.-CHEM. DR.RER.NAT. TAUCHNER, P., |
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8328 | Change in the person/name/address of the agent |
Free format text: TAUCHNER, P., DIPL.-CHEM. DR.RER.NAT. HEUNEMANN, D., DIPL.-PHYS. DR.RER.NAT., PAT.-ANWAELTE, 8000 MUENCHEN |
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