JP2003519207A - トルテロジンおよびその類似体の調製方法ならびにこの方法で調製される中間体 - Google Patents
トルテロジンおよびその類似体の調製方法ならびにこの方法で調製される中間体Info
- Publication number
- JP2003519207A JP2003519207A JP2001550189A JP2001550189A JP2003519207A JP 2003519207 A JP2003519207 A JP 2003519207A JP 2001550189 A JP2001550189 A JP 2001550189A JP 2001550189 A JP2001550189 A JP 2001550189A JP 2003519207 A JP2003519207 A JP 2003519207A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- formula
- enantiomers
- enriched
- defined above
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims abstract description 31
- OOGJQPCLVADCPB-HXUWFJFHSA-N tolterodine Chemical compound C1([C@@H](CCN(C(C)C)C(C)C)C=2C(=CC=C(C)C=2)O)=CC=CC=C1 OOGJQPCLVADCPB-HXUWFJFHSA-N 0.000 title claims abstract description 23
- 229960004045 tolterodine Drugs 0.000 title claims abstract description 19
- BDIAUFOIMFAIPU-UHFFFAOYSA-N valepotriate Natural products CC(C)CC(=O)OC1C=C(C(=COC2OC(=O)CC(C)C)COC(C)=O)C2C11CO1 BDIAUFOIMFAIPU-UHFFFAOYSA-N 0.000 title claims abstract description 19
- 238000002360 preparation method Methods 0.000 title abstract description 4
- 239000000543 intermediate Substances 0.000 title abstract description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 84
- 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 abstract description 29
- 150000003839 salts Chemical class 0.000 claims abstract description 28
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
- 239000001257 hydrogen Substances 0.000 claims abstract description 9
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 7
- 150000002367 halogens Chemical class 0.000 claims abstract description 7
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 7
- -1 methoxy, hydroxy, hydroxymethyl Chemical group 0.000 claims abstract description 6
- 230000003647 oxidation Effects 0.000 claims abstract description 6
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 6
- 230000008707 rearrangement Effects 0.000 claims abstract description 5
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims abstract description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 7
- 230000009467 reduction Effects 0.000 claims description 7
- 238000006722 reduction reaction Methods 0.000 claims description 7
- 230000002829 reductive effect Effects 0.000 claims description 7
- 150000001412 amines Chemical class 0.000 claims description 6
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 6
- 150000002440 hydroxy compounds Chemical class 0.000 claims description 5
- 238000006268 reductive amination reaction Methods 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 238000007363 ring formation reaction Methods 0.000 claims description 2
- 239000002585 base Substances 0.000 abstract description 5
- 239000012458 free base Substances 0.000 abstract description 2
- 239000007858 starting material Substances 0.000 abstract description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 20
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 239000000126 substance Substances 0.000 description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 6
- 150000002596 lactones Chemical class 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 5
- 238000003818 flash chromatography Methods 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 5
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 4
- 238000010828 elution Methods 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- SUHIZPDCJOQZLN-UHFFFAOYSA-N 6-methyl-4-phenyl-3,4-dihydrochromen-2-one Chemical compound C12=CC(C)=CC=C2OC(=O)CC1C1=CC=CC=C1 SUHIZPDCJOQZLN-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000012973 diazabicyclooctane Substances 0.000 description 3
- QNXSIUBBGPHDDE-UHFFFAOYSA-N indan-1-one Chemical compound C1=CC=C2C(=O)CCC2=C1 QNXSIUBBGPHDDE-UHFFFAOYSA-N 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- QFMZQPDHXULLKC-UHFFFAOYSA-N 1,2-bis(diphenylphosphino)ethane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCP(C=1C=CC=CC=1)C1=CC=CC=C1 QFMZQPDHXULLKC-UHFFFAOYSA-N 0.000 description 2
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 229910000085 borane Inorganic materials 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 229940043279 diisopropylamine Drugs 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- PUPAWTXNPAJCHR-UHFFFAOYSA-N oxazaborole Chemical compound O1C=CB=N1 PUPAWTXNPAJCHR-UHFFFAOYSA-N 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- WEKSEMHQTYUZNT-INIZCTEOSA-N (1s)-5-methyl-3-phenyl-1h-inden-1-ol Chemical compound C([C@H](O)C1=CC=C(C=C11)C)=C1C1=CC=CC=C1 WEKSEMHQTYUZNT-INIZCTEOSA-N 0.000 description 1
- SBTVLCPCSXMWIQ-UHFFFAOYSA-N (3,5-dimethylphenyl) carbamate Chemical compound CC1=CC(C)=CC(OC(N)=O)=C1 SBTVLCPCSXMWIQ-UHFFFAOYSA-N 0.000 description 1
- UNZRAQRBZKGSJG-DZWUOMMKSA-N (3s)-5-methyl-3-phenyl-2,3-dihydroinden-1-one;(1s)-5-methyl-3-phenyl-1h-inden-1-ol Chemical compound C1([C@@H]2CC(=O)C3=CC=C(C=C32)C)=CC=CC=C1.C([C@H](O)C1=CC=C(C=C11)C)=C1C1=CC=CC=C1 UNZRAQRBZKGSJG-DZWUOMMKSA-N 0.000 description 1
- VKMBFNPCOUOTLF-GBLKILIMSA-N (4S)-6-methyl-4-phenyl-3,4-dihydrochromen-2-one (3S)-5-methyl-3-phenyl-2,3-dihydroinden-1-one Chemical compound CC=1C=C2[C@@H](CC(C2=CC1)=O)C1=CC=CC=C1.CC=1C=C2[C@@H](CC(OC2=CC1)=O)C1=CC=CC=C1 VKMBFNPCOUOTLF-GBLKILIMSA-N 0.000 description 1
- JGRSOLBFAHJDTL-KNVGNIICSA-N (4s)-6-methyl-4-phenyl-3,4-dihydro-2h-chromen-2-ol Chemical compound C1([C@@H]2CC(O)OC3=CC=C(C=C32)C)=CC=CC=C1 JGRSOLBFAHJDTL-KNVGNIICSA-N 0.000 description 1
- SUHIZPDCJOQZLN-ZDUSSCGKSA-N (4s)-6-methyl-4-phenyl-3,4-dihydrochromen-2-one Chemical compound C1([C@@H]2CC(=O)OC3=CC=C(C=C32)C)=CC=CC=C1 SUHIZPDCJOQZLN-ZDUSSCGKSA-N 0.000 description 1
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 description 1
- KRVGXFREOJHJAX-UHFFFAOYSA-N 2-bromo-1-(4-methylphenyl)ethanone Chemical compound CC1=CC=C(C(=O)CBr)C=C1 KRVGXFREOJHJAX-UHFFFAOYSA-N 0.000 description 1
- IHULIZVDVYDOPA-UHFFFAOYSA-N 2-phenylinden-1-one Chemical compound C=1C2=CC=CC=C2C(=O)C=1C1=CC=CC=C1 IHULIZVDVYDOPA-UHFFFAOYSA-N 0.000 description 1
- MZFIOCKXBSMAKY-UHFFFAOYSA-N 3-(3-phenylprop-2-enoyl)-1,3-oxazolidin-2-one Chemical compound C1COC(=O)N1C(=O)C=CC1=CC=CC=C1 MZFIOCKXBSMAKY-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- VDQMHHMZXNDCBD-UHFFFAOYSA-N 5-methyl-3-phenylinden-1-one Chemical compound C12=CC(C)=CC=C2C(=O)C=C1C1=CC=CC=C1 VDQMHHMZXNDCBD-UHFFFAOYSA-N 0.000 description 1
- 101100000419 Autographa californica nuclear polyhedrosis virus AC41 gene Proteins 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 241001000171 Chira Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- DUXZAXCGJSBGDW-HXUWFJFHSA-N Desfesoterodine Chemical compound C1([C@@H](CCN(C(C)C)C(C)C)C=2C(=CC=C(CO)C=2)O)=CC=CC=C1 DUXZAXCGJSBGDW-HXUWFJFHSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 230000005526 G1 to G0 transition Effects 0.000 description 1
- 208000018522 Gastrointestinal disease Diseases 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 101150003085 Pdcl gene Proteins 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 206010046543 Urinary incontinence Diseases 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 1
- UORVGPXVDQYIDP-BJUDXGSMSA-N borane Chemical class [10BH3] UORVGPXVDQYIDP-BJUDXGSMSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- ODWXUNBKCRECNW-UHFFFAOYSA-M bromocopper(1+) Chemical compound Br[Cu+] ODWXUNBKCRECNW-UHFFFAOYSA-M 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013583 drug formulation Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 235000011087 fumaric acid Nutrition 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- CWCFLMZNJOMUCN-UHFFFAOYSA-M magnesium;1-methoxy-4-methylbenzene-6-ide;bromide Chemical compound [Mg+2].[Br-].COC1=CC=C(C)C=[C-]1 CWCFLMZNJOMUCN-UHFFFAOYSA-M 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- BDOLXPFAFMNDOK-UHFFFAOYSA-N oxazaborolidine Chemical compound B1CCON1 BDOLXPFAFMNDOK-UHFFFAOYSA-N 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- MUJIDPITZJWBSW-UHFFFAOYSA-N palladium(2+) Chemical compound [Pd+2] MUJIDPITZJWBSW-UHFFFAOYSA-N 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000006462 rearrangement reaction Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000002485 urinary effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
- C07D311/20—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 hydrogenated in the hetero ring
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy 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
- C07C215/48—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 amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by hydroxy groups
- C07C215/54—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 amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by hydroxy groups linked by carbon chains having at least three carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/143—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of ketones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C35/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C35/22—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system
- C07C35/23—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system with hydroxy on a condensed ring system having two rings
- C07C35/32—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system with hydroxy on a condensed ring system having two rings the condensed ring system being a (4.3.0) system, e.g. indenols
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
- C07C45/512—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being a free hydroxyl group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/65—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
- C07C45/74—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups combined with dehydration
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/82—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups
- C07C49/835—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups having unsaturation outside an aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
-
- 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
- C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
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- Chemical & Material Sciences (AREA)
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- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Urology & Nephrology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pyrane Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE9904850A SE9904850D0 (sv) | 1999-12-30 | 1999-12-30 | Novel process and intermediates |
| SE9904850-6 | 1999-12-30 | ||
| PCT/SE2000/002662 WO2001049649A1 (en) | 1999-12-30 | 2000-12-22 | Process of preparing tolterodine and analogues there of as well as intermediates prepared in the process |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2003519207A true JP2003519207A (ja) | 2003-06-17 |
| JP2003519207A5 JP2003519207A5 (enExample) | 2007-12-06 |
Family
ID=20418365
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001550189A Pending JP2003519207A (ja) | 1999-12-30 | 2000-12-22 | トルテロジンおよびその類似体の調製方法ならびにこの方法で調製される中間体 |
Country Status (29)
| Country | Link |
|---|---|
| US (1) | US6310248B2 (enExample) |
| EP (2) | EP1242361B1 (enExample) |
| JP (1) | JP2003519207A (enExample) |
| KR (1) | KR20020062669A (enExample) |
| CN (1) | CN1209342C (enExample) |
| AR (1) | AR027138A1 (enExample) |
| AT (1) | ATE282019T1 (enExample) |
| AU (1) | AU782796B2 (enExample) |
| BR (1) | BR0016785A (enExample) |
| CA (1) | CA2392832A1 (enExample) |
| CZ (1) | CZ20022255A3 (enExample) |
| DE (1) | DE60015799T2 (enExample) |
| DK (1) | DK1242361T3 (enExample) |
| EE (1) | EE200200325A (enExample) |
| ES (1) | ES2228658T3 (enExample) |
| HU (1) | HUP0203816A3 (enExample) |
| IL (1) | IL150275A0 (enExample) |
| MX (1) | MXPA02006415A (enExample) |
| MY (1) | MY118906A (enExample) |
| NO (1) | NO20023189L (enExample) |
| NZ (1) | NZ519079A (enExample) |
| PE (1) | PE20011123A1 (enExample) |
| PL (1) | PL355947A1 (enExample) |
| PT (1) | PT1242361E (enExample) |
| SE (1) | SE9904850D0 (enExample) |
| SK (1) | SK9392002A3 (enExample) |
| TW (1) | TWI225476B (enExample) |
| WO (1) | WO2001049649A1 (enExample) |
| ZA (1) | ZA200204066B (enExample) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006160622A (ja) * | 2004-12-03 | 2006-06-22 | Sumitomo Chemical Co Ltd | トルテロジンの製造方法 |
| JP2007515459A (ja) * | 2003-12-22 | 2007-06-14 | ラガクティブス,エス.エル. | トルテロジンを得るための方法 |
| WO2012063843A1 (ja) * | 2010-11-09 | 2012-05-18 | 株式会社カネカ | ハロゲン化インデノン類及びそれを用いた光学活性インダノン類又は光学活性インダノール類の製造方法 |
| KR20150097511A (ko) * | 2012-12-19 | 2015-08-26 | 하. 룬드벡 아크티에셀스카브 | 6-클로로-3-(페닐-d5)-인덴-1-온 및 이의 용도 |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0957073A1 (en) * | 1998-05-12 | 1999-11-17 | Schwarz Pharma Ag | Novel derivatives of 3,3-diphenylpropylamines |
| US6703504B2 (en) | 2002-02-11 | 2004-03-09 | Clarke Slemon | Conformationally constrained compounds as dendrimer cores |
| WO2003064501A1 (en) * | 2002-01-31 | 2003-08-07 | Clarke Slemon | Conformationally restricted compounds as dendrimer cores |
| EP1424079A1 (en) * | 2002-11-27 | 2004-06-02 | Boehringer Ingelheim International GmbH | Combination of a beta-3-receptor agonist and of a reuptake inhibitor of serotonin and/or norepinephrine |
| DE10315917A1 (de) * | 2003-04-08 | 2004-11-18 | Schwarz Pharma Ag | Hochreine Basen von 3,3-Diphenylpropylaminmonoestern |
| ITMI20031354A1 (it) * | 2003-07-02 | 2005-01-03 | Istituto Di Chimica Biomolecolare D El Cnr Sezione | Sintesis enantioselettiva di composti enantiomericamente arricchiti. |
| ITMI20040616A1 (it) * | 2004-03-30 | 2004-06-30 | Dinamite Dipharma S P A In For | Processo per la preparazione di tolterodina e suoi intermedi |
| EP1629834A1 (en) | 2004-08-27 | 2006-03-01 | KRKA, D.D., Novo Mesto | Sustained release pharmaceutical composition of tolterodine |
| ITMI20041920A1 (it) * | 2004-10-11 | 2005-01-11 | Chemi Spa | Processo per la preparazione di n, n-diisopropil-3-2-idrossi-5-metilfenil-3-fenil-propabammina |
| US20080045602A1 (en) * | 2004-12-24 | 2008-02-21 | Casar Renata T | Process for Preparation of 3-(2-Hydroxy-5Methylphenyl)-N, N-Disopropyl-3-Phenylpropylamine |
| US7528267B2 (en) * | 2005-08-01 | 2009-05-05 | Girindus America, Inc. | Method for enantioselective hydrogenation of chromenes |
| ES2268987B1 (es) | 2005-08-05 | 2008-02-01 | Ragactives, S.L. | Procedimiento para la obtencion de 3,3-difenilpropilaminas. |
| KR100647068B1 (ko) | 2005-09-15 | 2006-11-23 | 하나제약 주식회사 | 라세믹n,n-디이소프로필-3-(2-히드록시-5-메틸페닐)-3-페닐프로판아민의 제조방법 |
| KR100686351B1 (ko) * | 2006-01-12 | 2007-02-22 | 주식회사 카이로제닉스 | 톨테로딘 라세미체의 제조방법 |
| DK2029567T3 (da) | 2006-05-24 | 2010-11-29 | Pfizer Ltd | Fremgangsmåde til frembringelse af benzopyran-2-ol-derivater |
| SI2027103T1 (sl) | 2006-06-12 | 2014-07-31 | Ucb Pharma Gmbh | Novi kiralni vmesni produkt, postopek za njegovo proizvodnjo in njega uporaba pri proizvodnji tolterodina, fesoterodina ali njih aktivnega metabolita |
| KR100717361B1 (ko) * | 2006-08-07 | 2007-05-11 | 주식회사 카이로제닉스 | 톨테로딘 라세미체 및 이의 중간체의 제조방법 |
| US8871275B2 (en) | 2007-08-08 | 2014-10-28 | Inventia Healthcare Private Limited | Extended release compositions comprising tolterodine |
| HRP20140640T1 (hr) | 2008-08-19 | 2014-11-21 | Xenoport, Inc. | Prolijekovi monometil estera fumarne kiseline, farmaceutski sastavi iz toga i postupci njihove uporabe |
| CA2748250A1 (en) | 2008-12-24 | 2010-07-01 | Daiichi Sankyo Company, Limited | Indanyl compounds |
| MX2011006655A (es) | 2008-12-24 | 2011-07-29 | Daiichi Sankyo Co Ltd | Compuestos de anima ciclica. |
| KR101275984B1 (ko) * | 2010-10-18 | 2013-06-18 | 경기대학교 산학협력단 | 광학활성을 갖는 크로만계 유도체 및 이의 제조방법 |
| EP2476665A1 (en) | 2011-01-17 | 2012-07-18 | Cambrex Profarmaco Milano S.r.l. | Process for the preparation of N,N-diisopropyl-3-(2-hydroxy-5-methylphenyl)- 3-phenyl propylamine and its salts starting from a novel intermediate |
| WO2012098044A1 (en) | 2011-01-17 | 2012-07-26 | Cambrex Profarmaco Milano S.R.L. | Process for the preparation of n,n-diisopropyl-3-(2-hydroxy-5-methylphenyl)- 3-phenyl propylamine and its salts starting from a novel intermediate |
| PE20150928A1 (es) | 2011-06-20 | 2015-06-26 | Lundbeck & Co As H | 1-piperazino-3-fenil-indanos deuterados para el tratamiento de esquizofrenia |
| CN103159657B (zh) * | 2011-12-08 | 2016-06-29 | 重庆华邦胜凯制药有限公司 | 一种定向合成不饱和共轭醇的方法 |
| KR101380982B1 (ko) | 2013-04-29 | 2014-04-10 | 경기대학교 산학협력단 | 광학활성을 갖는 크로만-2-올 유도체 및 이의 제조방법 |
| WO2017137955A1 (en) | 2016-02-14 | 2017-08-17 | Celestis Pharmaceuticals Pvt. Ltd. | Novel (r) and rac 3-(2-(allyloxy)-5-methylphenyl)-n,n-diisopropyl-3- phenylpropan-1-amine and its use for synthesis of (r) and rac-2-(3- (diisopropylamino)-1-phenylpropyl)-4-(hydroxymethyl)phenol |
| US20210282443A1 (en) * | 2016-07-12 | 2021-09-16 | Chromocell Corporation | Compounds, compositions, and methods for modulating sweet taste |
| WO2020114853A1 (en) | 2018-12-03 | 2020-06-11 | H. Lundbeck A/S | Prodrugs of 4-((1r,3s)-6-chloro-3-phenyl-2,3-dihydro-1h-inden-1-yl)-1,2,2-trimethylpiperazine and 4-((1/r,3s)-6-chloro-3-(phenyl-d5)-2,3-dihydro-1h-inden-1-yl)-2,2-dimethy-1-(methyl-d3)piperazine |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH03503163A (ja) * | 1988-01-22 | 1991-07-18 | フアーマシア・アンド・アツプジヨン・アー・ベー | 新規アミン、その使用及び製法 |
| JPH08503208A (ja) * | 1992-11-06 | 1996-04-09 | フアーマシア・アー・ベー | 新規な3,3−ジフェニルプロピルアミン類、その使用および製造法 |
| JP2001507691A (ja) * | 1996-12-31 | 2001-06-12 | ファルマシア・アンド・アップジョン・カンパニー | トルテロジンの製法 |
| JP2003519079A (ja) * | 1998-05-12 | 2003-06-17 | シュヴァルツ・ファルマ・アクチエンゲゼルシャフト | 3,3−ジフェニルプロピルアミンの新規な誘導体 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA969363B (en) | 1995-11-08 | 1997-11-18 | Smithkline Beecham Corp | An improved process for preparing aromatic ring-fused cyclopentane derivatives. |
-
1999
- 1999-12-30 SE SE9904850A patent/SE9904850D0/xx unknown
-
2000
- 2000-12-20 MY MYPI20005976A patent/MY118906A/en unknown
- 2000-12-22 HU HU0203816A patent/HUP0203816A3/hu unknown
- 2000-12-22 PT PT00990151T patent/PT1242361E/pt unknown
- 2000-12-22 DE DE60015799T patent/DE60015799T2/de not_active Expired - Lifetime
- 2000-12-22 EE EEP200200325A patent/EE200200325A/xx unknown
- 2000-12-22 EP EP00990151A patent/EP1242361B1/en not_active Expired - Lifetime
- 2000-12-22 PL PL00355947A patent/PL355947A1/xx not_active Application Discontinuation
- 2000-12-22 AU AU27190/01A patent/AU782796B2/en not_active Ceased
- 2000-12-22 CZ CZ20022255A patent/CZ20022255A3/cs unknown
- 2000-12-22 CN CNB008180067A patent/CN1209342C/zh not_active Expired - Fee Related
- 2000-12-22 SK SK939-2002A patent/SK9392002A3/sk unknown
- 2000-12-22 JP JP2001550189A patent/JP2003519207A/ja active Pending
- 2000-12-22 NZ NZ519079A patent/NZ519079A/en unknown
- 2000-12-22 EP EP04014454A patent/EP1496045A3/en not_active Withdrawn
- 2000-12-22 MX MXPA02006415A patent/MXPA02006415A/es active IP Right Grant
- 2000-12-22 AT AT00990151T patent/ATE282019T1/de not_active IP Right Cessation
- 2000-12-22 ES ES00990151T patent/ES2228658T3/es not_active Expired - Lifetime
- 2000-12-22 US US09/748,042 patent/US6310248B2/en not_active Expired - Fee Related
- 2000-12-22 KR KR1020027008466A patent/KR20020062669A/ko not_active Withdrawn
- 2000-12-22 CA CA002392832A patent/CA2392832A1/en not_active Abandoned
- 2000-12-22 DK DK00990151T patent/DK1242361T3/da active
- 2000-12-22 WO PCT/SE2000/002662 patent/WO2001049649A1/en not_active Ceased
- 2000-12-22 IL IL15027500A patent/IL150275A0/xx unknown
- 2000-12-22 BR BR0016785-1A patent/BR0016785A/pt active Search and Examination
- 2000-12-27 PE PE2000001404A patent/PE20011123A1/es not_active Application Discontinuation
- 2000-12-28 TW TW089128081A patent/TWI225476B/zh active
- 2000-12-28 AR ARP000106999A patent/AR027138A1/es unknown
-
2002
- 2002-05-22 ZA ZA200204066A patent/ZA200204066B/en unknown
- 2002-07-01 NO NO20023189A patent/NO20023189L/no not_active Application Discontinuation
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH03503163A (ja) * | 1988-01-22 | 1991-07-18 | フアーマシア・アンド・アツプジヨン・アー・ベー | 新規アミン、その使用及び製法 |
| JPH08503208A (ja) * | 1992-11-06 | 1996-04-09 | フアーマシア・アー・ベー | 新規な3,3−ジフェニルプロピルアミン類、その使用および製造法 |
| JP2001507691A (ja) * | 1996-12-31 | 2001-06-12 | ファルマシア・アンド・アップジョン・カンパニー | トルテロジンの製法 |
| JP2003519079A (ja) * | 1998-05-12 | 2003-06-17 | シュヴァルツ・ファルマ・アクチエンゲゼルシャフト | 3,3−ジフェニルプロピルアミンの新規な誘導体 |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007515459A (ja) * | 2003-12-22 | 2007-06-14 | ラガクティブス,エス.エル. | トルテロジンを得るための方法 |
| JP4874122B2 (ja) * | 2003-12-22 | 2012-02-15 | ラガクティブス,エス.エル. | トルテロジンを得るための方法 |
| JP2006160622A (ja) * | 2004-12-03 | 2006-06-22 | Sumitomo Chemical Co Ltd | トルテロジンの製造方法 |
| WO2012063843A1 (ja) * | 2010-11-09 | 2012-05-18 | 株式会社カネカ | ハロゲン化インデノン類及びそれを用いた光学活性インダノン類又は光学活性インダノール類の製造方法 |
| JP2016074712A (ja) * | 2010-11-09 | 2016-05-12 | 株式会社カネカ | エノン化合物 |
| JP5941410B2 (ja) * | 2010-11-09 | 2016-06-29 | 株式会社カネカ | ハロゲン化インデノン類及びそれを用いた光学活性インダノン類又は光学活性インダノール類の製造方法 |
| KR20150097511A (ko) * | 2012-12-19 | 2015-08-26 | 하. 룬드벡 아크티에셀스카브 | 6-클로로-3-(페닐-d5)-인덴-1-온 및 이의 용도 |
| JP2016501901A (ja) * | 2012-12-19 | 2016-01-21 | ハー・ルンドベック・アクチエゼルスカベット | 6−クロロ−3−(フェニル−d5)インデン−1−オンおよびその使用 |
| KR102212096B1 (ko) * | 2012-12-19 | 2021-02-04 | 하. 룬드벡 아크티에셀스카브 | 6-클로로-3-(페닐-d5)-인덴-1-온 및 이의 용도 |
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