SE409699B - Forfarande for framstellning av nya bensylaminer - Google Patents

Forfarande for framstellning av nya bensylaminer

Info

Publication number: SE409699B
Authority: SE; Sweden
Prior art keywords: hydroxy; group; dibromo; general formula; benzylamine
Prior art date: 1972-10-23

Application number

SE7314321A

Other languages

English (en)

Swedish (sv)

Inventor

J Keck

S Puschmann

G Kruger

K-R Noll

Original Assignee

Thomae Gmbh Dr K

Priority date (The priority date 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 date listed.)

1972-10-23

Filing date

1973-10-22

Publication date

1979-09-03

1972-10-23 Priority claimed from DE19722251891 external-priority patent/DE2251891C3/de

1973-04-02 Priority claimed from DE2316325A external-priority patent/DE2316325A1/de

1973-07-26 Priority claimed from DE19732337932 external-priority patent/DE2337932A1/de

1973-09-17 Priority claimed from DE2346743A external-priority patent/DE2346743C3/de

1973-10-22 Application filed by Thomae Gmbh Dr K filed Critical Thomae Gmbh Dr K

1979-09-03 Publication of SE409699B publication Critical patent/SE409699B/sv

Links

238000000034 method Methods 0.000 title claims description 23
150000003939 benzylamines Chemical class 0.000 title claims 2
238000004519 manufacturing process Methods 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims description 65
-1 sulfonyloxy Chemical group 0.000 claims description 59
238000006243 chemical reaction Methods 0.000 claims description 40
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 38
229910052739 hydrogen Inorganic materials 0.000 claims description 33
239000001257 hydrogen Substances 0.000 claims description 33
239000002904 solvent Substances 0.000 claims description 31
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 30
229910052794 bromium Inorganic materials 0.000 claims description 28
125000000217 alkyl group Chemical group 0.000 claims description 27
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 26
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 24
125000004432 carbon atom Chemical group C* 0.000 claims description 22
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 22
238000002360 preparation method Methods 0.000 claims description 21
239000002253 acid Substances 0.000 claims description 20
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 19
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 19
235000019253 formic acid Nutrition 0.000 claims description 19
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 18
150000001412 amines Chemical class 0.000 claims description 18
238000009835 boiling Methods 0.000 claims description 13
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 12
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 12
239000007795 chemical reaction product Substances 0.000 claims description 12
125000006239 protecting group Chemical group 0.000 claims description 12
229930040373 Paraformaldehyde Natural products 0.000 claims description 11
229920002866 paraformaldehyde Polymers 0.000 claims description 11
239000000460 chlorine Substances 0.000 claims description 10
229910052801 chlorine Inorganic materials 0.000 claims description 10
150000002431 hydrogen Chemical group 0.000 claims description 10
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 8
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 7
230000007062 hydrolysis Effects 0.000 claims description 7
238000006460 hydrolysis reaction Methods 0.000 claims description 7
229910052987 metal hydride Inorganic materials 0.000 claims description 7
150000004681 metal hydrides Chemical class 0.000 claims description 7
239000011541 reaction mixture Substances 0.000 claims description 7
150000003839 salts Chemical class 0.000 claims description 7
YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical compound [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 claims description 6
125000003710 aryl alkyl group Chemical group 0.000 claims description 6
125000002843 carboxylic acid group Chemical group 0.000 claims description 6
239000003054 catalyst Substances 0.000 claims description 6
238000003776 cleavage reaction Methods 0.000 claims description 6
125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 6
230000007017 scission Effects 0.000 claims description 6
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 5
150000001408 amides Chemical class 0.000 claims description 5
235000019270 ammonium chloride Nutrition 0.000 claims description 5
125000003118 aryl group Chemical group 0.000 claims description 5
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
238000010438 heat treatment Methods 0.000 claims description 5
150000007522 mineralic acids Chemical class 0.000 claims description 5
150000007524 organic acids Chemical class 0.000 claims description 5
235000005985 organic acids Nutrition 0.000 claims description 5
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 4
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 4
239000003377 acid catalyst Substances 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 4
125000004104 aryloxy group Chemical group 0.000 claims description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
150000004820 halides Chemical class 0.000 claims description 4
229910000042 hydrogen bromide Inorganic materials 0.000 claims description 4
229910052740 iodine Inorganic materials 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
229910052698 phosphorus Inorganic materials 0.000 claims description 4
239000011574 phosphorus Substances 0.000 claims description 4
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
125000002252 acyl group Chemical group 0.000 claims description 3
125000004423 acyloxy group Chemical group 0.000 claims description 3
125000003342 alkenyl group Chemical group 0.000 claims description 3
125000005586 carbonic acid group Chemical group 0.000 claims description 3
125000005843 halogen group Chemical group 0.000 claims description 3
239000002798 polar solvent Substances 0.000 claims description 3
230000002829 reductive effect Effects 0.000 claims description 3
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
125000001118 alkylidene group Chemical group 0.000 claims description 2
229910052782 aluminium Inorganic materials 0.000 claims description 2
125000003277 amino group Chemical group 0.000 claims description 2
239000007767 bonding agent Substances 0.000 claims description 2
125000000753 cycloalkyl group Chemical group 0.000 claims description 2
238000011065 in-situ storage Methods 0.000 claims description 2
239000011630 iodine Substances 0.000 claims description 2
150000002500 ions Chemical class 0.000 claims description 2
230000011987 methylation Effects 0.000 claims description 2
238000007069 methylation reaction Methods 0.000 claims description 2
150000002902 organometallic compounds Chemical class 0.000 claims description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
125000000542 sulfonic acid group Chemical group 0.000 claims description 2
108090000623 proteins and genes Proteins 0.000 claims 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 252
238000002844 melting Methods 0.000 description 219
230000008018 melting Effects 0.000 description 219
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 217
238000000354 decomposition reaction Methods 0.000 description 125
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 82
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 68
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 60
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 51
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 48
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 44
239000000203 mixture Substances 0.000 description 43
238000006722 reduction reaction Methods 0.000 description 41
239000000243 solution Substances 0.000 description 41
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 37
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 36
239000012279 sodium borohydride Substances 0.000 description 34
229910000033 sodium borohydride Inorganic materials 0.000 description 34
AGVKXDPPPSLISR-UHFFFAOYSA-N n-ethylcyclohexanamine Chemical compound CCNC1CCCCC1 AGVKXDPPPSLISR-UHFFFAOYSA-N 0.000 description 30
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 29
VAYGTMNZLZAUDL-UHFFFAOYSA-N 2,6-dibromo-4-(bromomethyl)phenol Chemical compound OC1=C(Br)C=C(CBr)C=C1Br VAYGTMNZLZAUDL-UHFFFAOYSA-N 0.000 description 27
SPUZPJKEJXIRSF-UHFFFAOYSA-N 2,4-dibromo-6-(bromomethyl)phenol Chemical compound OC1=C(Br)C=C(Br)C=C1CBr SPUZPJKEJXIRSF-UHFFFAOYSA-N 0.000 description 26
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 24
239000000499 gel Substances 0.000 description 22
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 22
239000002585 base Substances 0.000 description 20
CSKKJEAMSBKJFT-UHFFFAOYSA-N 2,4-dibromo-6-[[cyclohexyl(ethyl)amino]methyl]phenol Chemical compound C1CCCCC1N(CC)CC1=CC(Br)=CC(Br)=C1O CSKKJEAMSBKJFT-UHFFFAOYSA-N 0.000 description 19
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 19
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 18
229960000583 acetic acid Drugs 0.000 description 16
238000003756 stirring Methods 0.000 description 16
AXRZRBIBAABFEA-UHFFFAOYSA-N 2,4-dibromo-6-(hydroxymethyl)phenol Chemical compound OCC1=CC(Br)=CC(Br)=C1O AXRZRBIBAABFEA-UHFFFAOYSA-N 0.000 description 14
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical class OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 14
238000010992 reflux Methods 0.000 description 14
229910052938 sodium sulfate Inorganic materials 0.000 description 14
235000011152 sodium sulphate Nutrition 0.000 description 14
ZSVIBQBJUVMLCQ-UHFFFAOYSA-N 2,4-dibromo-6-[[cyclohexyl(ethyl)amino]methyl]phenol;hydrochloride Chemical compound Cl.C1CCCCC1N(CC)CC1=CC(Br)=CC(Br)=C1O ZSVIBQBJUVMLCQ-UHFFFAOYSA-N 0.000 description 13
239000012280 lithium aluminium hydride Substances 0.000 description 13
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
229910021529 ammonia Inorganic materials 0.000 description 12
GEDPQKGMHLHFOZ-XYPYZODXSA-N chembl2106163 Chemical compound C1C[C@@H](O)CC[C@@H]1NCC1=CC(Br)=CC(Br)=C1O GEDPQKGMHLHFOZ-XYPYZODXSA-N 0.000 description 12
239000002244 precipitate Substances 0.000 description 12
CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 12
IMLXLGZJLAOKJN-UHFFFAOYSA-N 4-aminocyclohexan-1-ol Chemical compound NC1CCC(O)CC1 IMLXLGZJLAOKJN-UHFFFAOYSA-N 0.000 description 11
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 11
241001465754 Metazoa Species 0.000 description 11
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
239000012362 glacial acetic acid Substances 0.000 description 11
239000000741 silica gel Substances 0.000 description 11
229910002027 silica gel Inorganic materials 0.000 description 11
239000000126 substance Substances 0.000 description 11
IYNVMUZHJUDFBD-UHFFFAOYSA-N 2-[(3,5-dibromo-2-hydroxyphenyl)methylamino]-2-methylpropane-1,1-diol Chemical compound OC(O)C(C)(C)NCC1=CC(Br)=CC(Br)=C1O IYNVMUZHJUDFBD-UHFFFAOYSA-N 0.000 description 10
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 10
239000013543 active substance Substances 0.000 description 10
239000012071 phase Substances 0.000 description 10
235000019439 ethyl acetate Nutrition 0.000 description 9
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 9
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 8
ZGDHUYVSPLAQKF-UHFFFAOYSA-N 2,6-dibromo-4-[[cyclohexyl(ethyl)amino]methyl]phenol;hydrochloride Chemical group Cl.C1CCCCC1N(CC)CC1=CC(Br)=C(O)C(Br)=C1 ZGDHUYVSPLAQKF-UHFFFAOYSA-N 0.000 description 8
KBXAJVONNDMLDG-UHFFFAOYSA-N 2-[(3,5-dibromo-2-hydroxyphenyl)methylamino]-2-methylpropane-1,1-diol;hydrochloride Chemical compound Cl.OC(O)C(C)(C)NCC1=CC(Br)=CC(Br)=C1O KBXAJVONNDMLDG-UHFFFAOYSA-N 0.000 description 8
NIQIPYGXPZUDDP-NTSWFWBYSA-N (1r,3s)-3-aminocyclohexan-1-ol Chemical compound N[C@H]1CCC[C@@H](O)C1 NIQIPYGXPZUDDP-NTSWFWBYSA-N 0.000 description 7
KLERNTFVTLXLIO-VHSXEESVSA-N 2,6-dibromo-4-[[[(1s,3r)-3-hydroxycyclohexyl]amino]methyl]phenol Chemical compound C1[C@H](O)CCC[C@@H]1NCC1=CC(Br)=C(O)C(Br)=C1 KLERNTFVTLXLIO-VHSXEESVSA-N 0.000 description 7
XTUVJUMINZSXGF-UHFFFAOYSA-N N-methylcyclohexylamine Chemical compound CNC1CCCCC1 XTUVJUMINZSXGF-UHFFFAOYSA-N 0.000 description 7
PAMIQIKDUOTOBW-UHFFFAOYSA-N N-methylcyclohexylamine Natural products CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 7
238000001816 cooling Methods 0.000 description 7
238000002425 crystallisation Methods 0.000 description 7
230000008025 crystallization Effects 0.000 description 7
239000012074 organic phase Substances 0.000 description 7
238000000527 sonication Methods 0.000 description 7
UOJKSRWAJLJIOJ-UHFFFAOYSA-N 2,6-dibromo-4-(hydroxymethyl)phenol Chemical compound OCC1=CC(Br)=C(O)C(Br)=C1 UOJKSRWAJLJIOJ-UHFFFAOYSA-N 0.000 description 6
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 6
230000002378 acidificating effect Effects 0.000 description 6
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 6
238000004440 column chromatography Methods 0.000 description 6
230000026030 halogenation Effects 0.000 description 6
238000005658 halogenation reaction Methods 0.000 description 6
DMIUTENHPOZESC-UHFFFAOYSA-N n,n-dihydroxy-2-methylpropan-2-amine Chemical compound CC(C)(C)N(O)O DMIUTENHPOZESC-UHFFFAOYSA-N 0.000 description 6
239000003921 oil Substances 0.000 description 6
GNIHGYYYCAZOCF-UHFFFAOYSA-N 2-(bromomethyl)-4,6-dichlorophenol Chemical compound OC1=C(Cl)C=C(Cl)C=C1CBr GNIHGYYYCAZOCF-UHFFFAOYSA-N 0.000 description 5
SRVXSISGYBMIHR-UHFFFAOYSA-N 3-[3-[3-(2-amino-2-oxoethyl)phenyl]-5-chlorophenyl]-3-(5-methyl-1,3-thiazol-2-yl)propanoic acid Chemical compound S1C(C)=CN=C1C(CC(O)=O)C1=CC(Cl)=CC(C=2C=C(CC(N)=O)C=CC=2)=C1 SRVXSISGYBMIHR-UHFFFAOYSA-N 0.000 description 5
RVELKTSHKDTMSZ-UHFFFAOYSA-N 4-(bromomethyl)-2,6-dichlorophenol Chemical compound OC1=C(Cl)C=C(CBr)C=C1Cl RVELKTSHKDTMSZ-UHFFFAOYSA-N 0.000 description 5
MKKSTJKBKNCMRV-UHFFFAOYSA-N 5-bromo-2-hydroxybenzaldehyde Chemical compound OC1=CC=C(Br)C=C1C=O MKKSTJKBKNCMRV-UHFFFAOYSA-N 0.000 description 5
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
230000000694 effects Effects 0.000 description 5
PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 5
239000011975 tartaric acid Substances 0.000 description 5
235000002906 tartaric acid Nutrition 0.000 description 5
ABDDQTDRAHXHOC-QMMMGPOBSA-N 1-[(7s)-5,7-dihydro-4h-thieno[2,3-c]pyran-7-yl]-n-methylmethanamine Chemical compound CNC[C@@H]1OCCC2=C1SC=C2 ABDDQTDRAHXHOC-QMMMGPOBSA-N 0.000 description 4
UHSJATMRCSZWEM-UHFFFAOYSA-N 2,4-dibromo-6-[[cyclohexyl(methyl)amino]methyl]phenol;hydrochloride Chemical compound Cl.C1CCCCC1N(C)CC1=CC(Br)=CC(Br)=C1O UHSJATMRCSZWEM-UHFFFAOYSA-N 0.000 description 4
FAXWFCTVSHEODL-UHFFFAOYSA-N 2,4-dibromophenol Chemical compound OC1=CC=C(Br)C=C1Br FAXWFCTVSHEODL-UHFFFAOYSA-N 0.000 description 4
KLERNTFVTLXLIO-UWVGGRQHSA-N 2,6-dibromo-4-[[[(1S,3S)-3-hydroxycyclohexyl]amino]methyl]phenol Chemical compound C1[C@@H](O)CCC[C@@H]1NCC1=CC(Br)=C(O)C(Br)=C1 KLERNTFVTLXLIO-UWVGGRQHSA-N 0.000 description 4
JHZOXYGFQMROFJ-UHFFFAOYSA-N 3,5-dibromo-2-hydroxybenzaldehyde Chemical compound OC1=C(Br)C=C(Br)C=C1C=O JHZOXYGFQMROFJ-UHFFFAOYSA-N 0.000 description 4
HORNXRXVQWOLPJ-UHFFFAOYSA-N 3-chlorophenol Chemical compound OC1=CC=CC(Cl)=C1 HORNXRXVQWOLPJ-UHFFFAOYSA-N 0.000 description 4
FUGKCSRLAQKUHG-UHFFFAOYSA-N 5-chloro-2-hydroxybenzaldehyde Chemical compound OC1=CC=C(Cl)C=C1C=O FUGKCSRLAQKUHG-UHFFFAOYSA-N 0.000 description 4
UERWSGAGIMZBJK-ZKCHVHJHSA-N CCN[C@H]1CC[C@H](O)CC1 Chemical compound CCN[C@H]1CC[C@H](O)CC1 UERWSGAGIMZBJK-ZKCHVHJHSA-N 0.000 description 4
BGRWLVRJIPTKQW-PFWPSKEQSA-N Cl.C1C[C@@H](O)CC[C@@H]1NCC1=CC(Br)=CC(Br)=C1O Chemical compound Cl.C1C[C@@H](O)CC[C@@H]1NCC1=CC(Br)=CC(Br)=C1O BGRWLVRJIPTKQW-PFWPSKEQSA-N 0.000 description 4
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 4
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
230000031709 bromination Effects 0.000 description 4
238000005893 bromination reaction Methods 0.000 description 4
239000013078 crystal Substances 0.000 description 4
239000000395 magnesium oxide Substances 0.000 description 4
CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-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
AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 4
YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 4
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
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150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
238000011097 chromatography purification Methods 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
229910017052 cobalt Inorganic materials 0.000 description 1
239000010941 cobalt Substances 0.000 description 1
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
239000000470 constituent Substances 0.000 description 1
YKFKEYKJGVSEIX-UHFFFAOYSA-N cyclohexanone, 4-(1,1-dimethylethyl)- Chemical compound CC(C)(C)C1CCC(=O)CC1 YKFKEYKJGVSEIX-UHFFFAOYSA-N 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
239000008298 dragée Substances 0.000 description 1
239000000975 dye Substances 0.000 description 1
HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
CHDFNIZLAAFFPX-UHFFFAOYSA-N ethoxyethane;oxolane Chemical compound CCOCC.C1CCOC1 CHDFNIZLAAFFPX-UHFFFAOYSA-N 0.000 description 1
HWJHWSBFPPPIPD-UHFFFAOYSA-N ethoxyethane;propan-2-one Chemical compound CC(C)=O.CCOCC HWJHWSBFPPPIPD-UHFFFAOYSA-N 0.000 description 1
239000000284 extract Substances 0.000 description 1
239000010643 fennel seed oil Substances 0.000 description 1
238000011049 filling Methods 0.000 description 1
235000013305 food Nutrition 0.000 description 1
238000005194 fractionation Methods 0.000 description 1
208000021302 gastroesophageal reflux disease Diseases 0.000 description 1
239000008103 glucose Substances 0.000 description 1
239000008187 granular material Substances 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
229920002674 hyaluronan Polymers 0.000 description 1
229960003160 hyaluronic acid Drugs 0.000 description 1
150000002466 imines Chemical class 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 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
239000000155 melt Substances 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
YSNXOQGDHGUKCZ-UHFFFAOYSA-N n-benzylhydroxylamine;hydron;chloride Chemical compound Cl.ONCC1=CC=CC=C1 YSNXOQGDHGUKCZ-UHFFFAOYSA-N 0.000 description 1
NVEYVSRXOFPIRE-UHFFFAOYSA-N n-cyclohexyl-n-methylacetamide Chemical compound CC(=O)N(C)C1CCCCC1 NVEYVSRXOFPIRE-UHFFFAOYSA-N 0.000 description 1
LRXSDHDEISIWQB-UHFFFAOYSA-N n-methylcycloheptanamine Chemical compound CNC1CCCCCC1 LRXSDHDEISIWQB-UHFFFAOYSA-N 0.000 description 1
SQGBZKZDUMBTIJ-UHFFFAOYSA-N n-prop-2-enylcyclohexanamine Chemical compound C=CCNC1CCCCC1 SQGBZKZDUMBTIJ-UHFFFAOYSA-N 0.000 description 1
QHZWWLYWZPCJMN-UHFFFAOYSA-N n-propylcycloheptanamine Chemical compound CCCNC1CCCCCC1 QHZWWLYWZPCJMN-UHFFFAOYSA-N 0.000 description 1
PXKCSKRXWAZGFK-UHFFFAOYSA-N n-propylcyclohexanamine Chemical compound CCCNC1CCCCC1 PXKCSKRXWAZGFK-UHFFFAOYSA-N 0.000 description 1
OPZNSPHUHIXVGR-UHFFFAOYSA-N n-propylcyclopentanamine Chemical compound CCCNC1CCCC1 OPZNSPHUHIXVGR-UHFFFAOYSA-N 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
230000036407 pain Effects 0.000 description 1
235000020030 perry Nutrition 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
LZMJNVRJMFMYQS-UHFFFAOYSA-N poseltinib Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(OC=C2)C2=N1 LZMJNVRJMFMYQS-UHFFFAOYSA-N 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
239000002243 precursor Substances 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
238000006268 reductive amination reaction Methods 0.000 description 1
238000007670 refining Methods 0.000 description 1
229940043230 sarcosine Drugs 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000002002 slurry Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000007921 spray Substances 0.000 description 1
230000001954 sterilising effect Effects 0.000 description 1
238000004659 sterilization and disinfection Methods 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
150000003613 toluenes Chemical class 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
230000001960 triggered effect Effects 0.000 description 1
238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Pulmonology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Engineering & Computer Science (AREA)
Life Sciences & Earth Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

SE7314321A 1972-10-23 1973-10-22 Forfarande for framstellning av nya bensylaminer SE409699B (sv)

Applications Claiming Priority (5)

Application Number	Priority Date	Filing Date	Title
DE19722251891 DE2251891C3 (de)		1972-10-23	Benzylamine, deren physiologisch verträglichen Salze, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel
DE2316325A DE2316325A1 (de)	1972-10-23	1973-04-02	Neue verfahren zur herstellung von benzylaminen
DE19732320967 DE2320967C3 (de)		1973-04-26	Neue Benzylamine, deren physiologisch verträgliche Salze, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel
DE19732337932 DE2337932A1 (de)	1972-10-23	1973-07-26	Neue verfahren zur herstellung von benzylaminen
DE2346743A DE2346743C3 (de)	1972-10-23	1973-09-17	2- oder 4-Hydroxy-3,5-dihalogenbenzylamine, deren physiologisch verträgliche Salze, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel

Publications (1)

Publication Number	Publication Date
SE409699B true SE409699B (sv)	1979-09-03

Family

ID=27510276

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SE7314321A SE409699B (sv)	1972-10-23	1973-10-22	Forfarande for framstellning av nya bensylaminer

Country Status (16)

Country	Link
JP (1)	JPS5535374B2 (es)
AT (1)	AT330149B (es)
BE (1)	BE806375A (es)
CA (1)	CA1092113A (es)
CH (11)	CH602575A5 (es)
DD (1)	DD108974A5 (es)
DK (1)	DK149883C (es)
FI (1)	FI62051C (es)
FR (1)	FR2203639B1 (es)
GB (1)	GB1450702A (es)
HU (1)	HU168131B (es)
IE (1)	IE38961B1 (es)
NL (1)	NL180978C (es)
NO (1)	NO138251C (es)
SE (1)	SE409699B (es)
SU (1)	SU530638A3 (es)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AT332863B (de) *	1973-01-02	1976-10-25	Gerot Pharmazeutika	Verfahren zur herstellung von neuen 2-aminomethyl-4,6-dihalogenphenolderivaten sowie deren additionssalzen mit sauren
DE2934508A1 (de) *	1978-09-06	1980-03-20	Sandoz Ag	Alpha -alkyl-o-oxybenzylamin- derivate, ihre herstellung und sie enthaltende heilmittel
US4578390A (en) *	1981-12-14	1986-03-25	Merck & Co., Inc.	Hydroxybenzylamino derivatives as anti-inflammatory agents
GB8606066D0 (en) *	1986-03-12	1986-04-16	Ici Plc	Bromine-containing polyols
DE3820292A1 (de) *	1988-06-15	1990-04-12	Basf Ag	Aminomethylphenole und diese enthaltende fungizide
EP2179651A4 (en) *	2007-06-29	2012-07-11	Sumitomo Chemical Co	MEANS FOR THE CONTROL OF PLANT DISEASES AND METHOD FOR THE CONTROL OF PLANT DISEASES
JP6683696B2 (ja) *	2014-11-05	2020-04-22	ダウグローバルテクノロジーズエルエルシー	難燃性ポリオール

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB836934A (en) *	1957-10-03	1960-06-09	Monsanto Chemicals	Phenolic amino compounds

1973
- 1973-10-16 NL NLAANVRAGE7314216,A patent/NL180978C/xx not_active IP Right Cessation
- 1973-10-19 SU SU1963879A patent/SU530638A3/ru active
- 1973-10-19 FI FI3254/73A patent/FI62051C/fi active
- 1973-10-22 BE BE136949A patent/BE806375A/xx not_active IP Right Cessation
- 1973-10-22 IE IE01888/73A patent/IE38961B1/xx unknown
- 1973-10-22 JP JP11886973A patent/JPS5535374B2/ja not_active Expired
- 1973-10-22 NO NO4087/73A patent/NO138251C/no unknown
- 1973-10-22 CA CA183,899A patent/CA1092113A/en not_active Expired
- 1973-10-22 HU HUTO938A patent/HU168131B/hu unknown
- 1973-10-22 SE SE7314321A patent/SE409699B/sv unknown
- 1973-10-22 DK DK571973A patent/DK149883C/da active
- 1973-10-23 CH CH1148377A patent/CH602575A5/xx not_active IP Right Cessation
- 1973-10-23 CH CH1148077A patent/CH602573A5/xx not_active IP Right Cessation
- 1973-10-23 CH CH1148277A patent/CH603550A5/xx not_active IP Right Cessation
- 1973-10-23 CH CH1148177A patent/CH602574A5/xx not_active IP Right Cessation
- 1973-10-23 CH CH1147977A patent/CH605621A5/xx not_active IP Right Cessation
- 1973-10-23 FR FR7337753A patent/FR2203639B1/fr not_active Expired
- 1973-10-23 CH CH1147677A patent/CH605620A5/xx not_active IP Right Cessation
- 1973-10-23 CH CH1147577A patent/CH602571A5/xx not_active IP Right Cessation
- 1973-10-23 CH CH1494973A patent/CH597148A5/xx not_active IP Right Cessation
- 1973-10-23 CH CH1147777A patent/CH611871A5/xx not_active IP Right Cessation
- 1973-10-23 CH CH1148477A patent/CH602576A5/xx not_active IP Right Cessation
- 1973-10-23 DD DD174238A patent/DD108974A5/xx unknown
- 1973-10-23 GB GB4933973A patent/GB1450702A/en not_active Expired
1975
- 1975-04-23 AT AT309675A patent/AT330149B/de not_active IP Right Cessation
1977
- 1977-09-20 CH CH1147877A patent/CH602572A5/xx not_active IP Right Cessation

Also Published As

Publication number	Publication date
SU530638A3 (ru)	1976-09-30
NL180978C (nl)	1987-06-01
CH605620A5 (es)	1978-09-29
NL7314216A (es)	1974-04-25
FR2203639B1 (es)	1978-02-03
CH597148A5 (es)	1978-03-31
DD108974A5 (es)	1974-10-12
FI62051B (fi)	1982-07-30
DK149883C (da)	1987-04-27
GB1450702A (en)	1976-09-29
IE38961L (en)	1974-04-23
HU168131B (es)	1976-02-28
FR2203639A1 (es)	1974-05-17
NL180978B (nl)	1987-01-02
JPS5535374B2 (es)	1980-09-12
AU6170273A (en)	1975-04-24
NO138251B (no)	1978-04-24
FI62051C (fi)	1982-11-10
CH603550A5 (es)	1978-08-31
CH602574A5 (es)	1978-07-31
NO138251C (no)	1978-08-02
DK149883B (da)	1986-10-20
JPS4972224A (es)	1974-07-12
CH602573A5 (es)	1978-07-31
BE806375A (fr)	1974-04-22
ATA309675A (de)	1975-09-15
AT330149B (de)	1976-06-10
CH602572A5 (es)	1978-07-31
IE38961B1 (en)	1978-07-05
CH602571A5 (es)	1978-07-31
CA1092113A (en)	1980-12-23
CH602575A5 (es)	1978-07-31
CH611871A5 (en)	1979-06-29
CH602576A5 (es)	1978-07-31
CH605621A5 (es)	1978-10-13

Publication	Publication Date	Title
RU2102387C1 (ru)	1998-01-20	Производные n-ацил-2,3-бензодиазепина, или их стереоизомеры, или кислые соли присоединения, обладающие биологической активностью, связанной с воздействием на центральную нервную систему, и фармакологически активная композиция на их основе
US4070484A (en)	1978-01-24	Antiallergic composition containing aromatic carboxylic amide derivatives and method of using the same
JPH03504010A (ja)	1991-09-05	ジベンゾフランカルボキサミド
SU997606A3 (ru)	1983-02-15	Способ получени производных простых ариловых эфиров или их фармацевтически приемлемых солей (его варианты)
Johnson et al.	1950	Ring closure of the 2-benzoylaminocyclohexanols. The mechanism of oxazoline formation
SE409699B (sv)	1979-09-03	Forfarande for framstellning av nya bensylaminer
DK150157B (da)	1986-12-22	Analogifremgangsmaade til fremstilling af furo-, thieno- eller pyrrolo (2,3-d)azepiner eller fysiologisk acceptable salte deraf med syrer eller baser
HU180240B (en)	1983-02-28	Process for producing new,substituted 1,3-diaryl-2-iminoimidasolidines and 2-imino-hexahydro-pyrimidines
JPS5867678A (ja)	1983-04-22	７―ブロム―５―（２―ハロゲンフェニル）―１ｈ―２，３―ジヒドロ―１，４―ベンゾジアゼピン―化合物、その製法及び該化合物を含有する中枢神経抑制剤
DE2441261A1 (de)	1976-03-18	Ringsubstituierte pyrazino-isochinolin-derivat und verfahren zu ihrer herstellung
US3177211A (en)	1965-04-06	10-[(aminocarbamyl-1-piperidyl)-loweralkyl]-phenothiazines
JPH072812A (ja)	1995-01-06	チアジアジノン
US4251534A (en)	1981-02-17	Antihypertensive polyfluorohydroxyisopropyl bicyclic and tricyclic carbostyrils
EP0000693B1 (de)	1980-07-23	Aminophenoxymethyl-2-morpholinderivate, ihre Herstellung und sie enthaltende Arzneimittel
US3953448A (en)	1976-04-27	Piperazino-anilido compounds
US3639423A (en)	1972-02-01	Tricyclic aminomethyl derivatives
EP0118565B1 (en)	1987-05-27	1,4-methano-2-benzazepine derivatives
US5229395A (en)	1993-07-20	Potential anticancer agents derived from acridine
JPS61126082A (ja)	1986-06-13	アミノピロリジン誘導体、そのエステルおよびその塩
NO800725L (no)	1980-10-13	Polysubstituerte diazatricycler.
US3396168A (en)	1968-08-06	Dibenzocycloheptane derivatives
US20030069417A1 (en)	2003-04-10	Novel synthesis and crystallization of piperazine ring-containing compounds
EP0127143B1 (en)	1990-03-21	Novel aryloxycycloalkanolaminoalkylene aryl ketones
PT93540A (pt)	1990-11-07	Processo para a preparacao de composicoes farmaceuticas contendo aminas policiclicas
EP0118566B1 (en)	1987-03-04	INDENO[1,2-b]PYRROLE DERIVATIVES