IL27887A - 1,1-diphenyl-2-methyl-3-(benzylidene amino) propanols - Google Patents
1,1-diphenyl-2-methyl-3-(benzylidene amino) propanolsInfo
- Publication number
- IL27887A IL27887A IL27887A IL2788767A IL27887A IL 27887 A IL27887 A IL 27887A IL 27887 A IL27887 A IL 27887A IL 2788767 A IL2788767 A IL 2788767A IL 27887 A IL27887 A IL 27887A
- Authority
- IL
- Israel
- Prior art keywords
- pheny
- ami
- methyl
- methy
- nopropanol
- Prior art date
Links
- BIWHCRMFAZGNGA-UHFFFAOYSA-N 3-(benzylideneamino)-2-methyl-1,1-diphenylpropan-1-ol Chemical class C=1C=CC=CC=1C(O)(C=1C=CC=CC=1)C(C)CN=CC1=CC=CC=C1 BIWHCRMFAZGNGA-UHFFFAOYSA-N 0.000 title 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 22
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 13
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 239000012442 inert solvent Substances 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 89
- 101150052863 THY1 gene Proteins 0.000 description 37
- 229960005335 propanol Drugs 0.000 description 24
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 239000000203 mixture Substances 0.000 description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- -1 BENZYLIDENE Chemical class 0.000 description 8
- 239000012965 benzophenone Substances 0.000 description 8
- MXZROAOUCUVNHX-UHFFFAOYSA-N 2-Aminopropanol Chemical compound CCC(N)O MXZROAOUCUVNHX-UHFFFAOYSA-N 0.000 description 7
- 229940024874 benzophenone Drugs 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 229940095076 benzaldehyde Drugs 0.000 description 6
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 239000000284 extract Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 101000881330 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) Dynein heavy chain, cytoplasmic Proteins 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- NVXKKAKSNWELHS-UHFFFAOYSA-N 3-hydroxy-2-methyl-3,3-diphenylpropanenitrile Chemical compound C=1C=CC=CC=1C(O)(C(C#N)C)C1=CC=CC=C1 NVXKKAKSNWELHS-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 150000004678 hydrides Chemical class 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- BZWGZQNUCNUCES-UHFFFAOYSA-N (2,3-dibromophenyl)-phenylmethanone Chemical compound BrC1=CC=CC(C(=O)C=2C=CC=CC=2)=C1Br BZWGZQNUCNUCES-UHFFFAOYSA-N 0.000 description 1
- HIKRJHFHGKZKRI-UHFFFAOYSA-N 2,4,6-Trimethylbenzaldehyde Natural products CC1=CC(C)=C(C=O)C(C)=C1 HIKRJHFHGKZKRI-UHFFFAOYSA-N 0.000 description 1
- LMUGWOGYBVBCTH-UHFFFAOYSA-N 2,4,6-trimethylbenzaldehyde Chemical compound CC1=CC(C)=C(C=O)C(C)=C1.CC1=CC(C)=C(C=O)C(C)=C1 LMUGWOGYBVBCTH-UHFFFAOYSA-N 0.000 description 1
- IBMUHJIDXFMZPI-UHFFFAOYSA-N 2-chlorobenzaldehyde Chemical compound ClC1=CC=CC=C1C=O.ClC1=CC=CC=C1C=O IBMUHJIDXFMZPI-UHFFFAOYSA-N 0.000 description 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
- ZOSTWKFQFNTANW-UHFFFAOYSA-N 2-cyclopentyl-n-naphthalen-2-yl-2-phenylacetamide Chemical compound C=1C=C2C=CC=CC2=CC=1NC(=O)C(C=1C=CC=CC=1)C1CCCC1 ZOSTWKFQFNTANW-UHFFFAOYSA-N 0.000 description 1
- NHSSTOSZJANVEV-UHFFFAOYSA-N 2-hydroxybutanenitrile Chemical compound CCC(O)C#N NHSSTOSZJANVEV-UHFFFAOYSA-N 0.000 description 1
- 125000006304 2-iodophenyl group Chemical group [H]C1=C([H])C(I)=C(*)C([H])=C1[H] 0.000 description 1
- SUISZCALMBHJQX-UHFFFAOYSA-N 3-bromobenzaldehyde Chemical compound BrC1=CC=CC(C=O)=C1 SUISZCALMBHJQX-UHFFFAOYSA-N 0.000 description 1
- YESCIRFCEGIMED-UHFFFAOYSA-N 3-butoxybenzaldehyde Chemical compound CCCCOC1=CC=CC(C=O)=C1 YESCIRFCEGIMED-UHFFFAOYSA-N 0.000 description 1
- VGJTVMOMWIKGSG-UHFFFAOYSA-N 3-hydroxy-2-methyl-3-phenylpropanenitrile Chemical compound N#CC(C)C(O)C1=CC=CC=C1 VGJTVMOMWIKGSG-UHFFFAOYSA-N 0.000 description 1
- COZQDNPLORIALF-UHFFFAOYSA-N 3-hydroxy-2-methylpropanenitrile Chemical compound OCC(C)C#N COZQDNPLORIALF-UHFFFAOYSA-N 0.000 description 1
- OKISUZLXOYGIFP-UHFFFAOYSA-N 4,4'-dichlorobenzophenone Chemical compound C1=CC(Cl)=CC=C1C(=O)C1=CC=C(Cl)C=C1 OKISUZLXOYGIFP-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- OPFTUNCRGUEPRZ-QLFBSQMISA-N Cyclohexane Natural products CC(=C)[C@@H]1CC[C@@](C)(C=C)[C@H](C(C)=C)C1 OPFTUNCRGUEPRZ-QLFBSQMISA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 208000007101 Muscle Cramp Diseases 0.000 description 1
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 239000002262 Schiff base Substances 0.000 description 1
- 150000004753 Schiff bases Chemical class 0.000 description 1
- 208000005392 Spasm Diseases 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 230000036528 appetite Effects 0.000 description 1
- 235000019789 appetite Nutrition 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 150000008366 benzophenones Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- QGPPRNDMALFDHJ-UHFFFAOYSA-N bis(2,4-dimethoxyphenyl)methanone Chemical compound COC1=CC(OC)=CC=C1C(=O)C1=CC=C(OC)C=C1OC QGPPRNDMALFDHJ-UHFFFAOYSA-N 0.000 description 1
- JCVYQVHAGOZGIX-UHFFFAOYSA-N bis(2-bromophenyl)methanone Chemical compound BrC1=CC=CC=C1C(=O)C1=CC=CC=C1Br JCVYQVHAGOZGIX-UHFFFAOYSA-N 0.000 description 1
- RFVHVYKVRGKLNK-UHFFFAOYSA-N bis(4-methoxyphenyl)methanone Chemical compound C1=CC(OC)=CC=C1C(=O)C1=CC=C(OC)C=C1 RFVHVYKVRGKLNK-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 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
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 235000019628 coolness Nutrition 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229960004756 ethanol Drugs 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical compound [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachlorophenol Chemical compound OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 description 1
- FTPZYWUJDVZEIE-UHFFFAOYSA-N phenyl-(2,4,5-trimethylphenyl)methanone Chemical compound C1=C(C)C(C)=CC(C)=C1C(=O)C1=CC=CC=C1 FTPZYWUJDVZEIE-UHFFFAOYSA-N 0.000 description 1
- HUCRPDCCPSDJHT-UHFFFAOYSA-N phenyl-(4-propoxyphenyl)methanone Chemical compound C1=CC(OCCC)=CC=C1C(=O)C1=CC=CC=C1 HUCRPDCCPSDJHT-UHFFFAOYSA-N 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000037047 psychomotor activity Effects 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/02—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups
- C07C251/24—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to carbon atoms of six-membered aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US554304A US3372193A (en) | 1966-06-01 | 1966-06-01 | 1, 1-diaryl-2-methyl-3-(benzylidene-amino) propan-(1)-ols |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IL27887A true IL27887A (en) | 1971-02-25 |
Family
ID=24212850
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL27887A IL27887A (en) | 1966-06-01 | 1967-04-30 | 1,1-diphenyl-2-methyl-3-(benzylidene amino) propanols |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3372193A (ref) |
| BE (1) | BE699337A (ref) |
| DE (1) | DE1643123A1 (ref) |
| DK (1) | DK114767B (ref) |
| ES (1) | ES340995A1 (ref) |
| GB (1) | GB1164898A (ref) |
| GR (1) | GR35226B (ref) |
| IL (1) | IL27887A (ref) |
| NL (1) | NL6707656A (ref) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8902209D0 (en) * | 1989-02-01 | 1989-03-22 | Wyeth John And Brother Limited | Preparation of cyclohexanol derivatives and novel thioamide intermediates |
| US7087765B2 (en) * | 1995-06-07 | 2006-08-08 | Nps Pharmaceuticals, Inc. | Compounds active at a novel site on receptor-operated calcium channels useful for treatment of neurological disorders and diseases |
| US6071970A (en) * | 1993-02-08 | 2000-06-06 | Nps Pharmaceuticals, Inc. | Compounds active at a novel site on receptor-operated calcium channels useful for treatment of neurological disorders and diseases |
| US6017965A (en) * | 1993-02-08 | 2000-01-25 | Nps Pharmaceuticals, Inc. | Compounds active at a novel site on receptor-operated calcium channels useful for treatment of neurological disorders and diseases |
| US6211245B1 (en) | 1993-02-08 | 2001-04-03 | Nps Pharmaceuticals, Inc. | Compounds active at a novel site on receptor-operated calcium channels useful for treatment of neurological disorders and diseases |
| US6750244B2 (en) | 1993-02-08 | 2004-06-15 | Nps Pharmaceuticals, Inc. | Compounds active at a novel site on receptor-operated calcium channels useful for treatment of neurological disorders and diseases |
| DE69434889D1 (de) | 1994-02-08 | 2007-01-11 | Nps Pharma Inc | An einer neuen Stelle von Rezeptorabhängigen Kalziumkanälen wirkende Verbindungen zur Behandlung von neurologischen Erkrankungen |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB811659A (en) * | 1955-07-05 | 1959-04-08 | Bayer Ag | Process for producing derivatives of 1-aryl-3-amino propanol-1 |
-
1966
- 1966-06-01 US US554304A patent/US3372193A/en not_active Expired - Lifetime
-
1967
- 1967-04-28 GB GB09672/67A patent/GB1164898A/en not_active Expired
- 1967-04-30 IL IL27887A patent/IL27887A/en unknown
- 1967-05-15 GR GR670135226A patent/GR35226B/el unknown
- 1967-05-25 DK DK274667AA patent/DK114767B/da unknown
- 1967-05-26 ES ES340995A patent/ES340995A1/es not_active Expired
- 1967-05-29 DE DE19671643123 patent/DE1643123A1/de active Pending
- 1967-06-01 BE BE699337D patent/BE699337A/xx unknown
- 1967-06-01 NL NL6707656A patent/NL6707656A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB1164898A (en) | 1969-09-24 |
| ES340995A1 (es) | 1968-06-16 |
| GR35226B (el) | 1968-08-28 |
| US3372193A (en) | 1968-03-05 |
| NL6707656A (ref) | 1967-12-04 |
| DK114767B (da) | 1969-08-04 |
| BE699337A (ref) | 1967-12-01 |
| DE1643123A1 (de) | 1971-01-14 |
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