DE2340629A1 - Tetrahydronaphthalinderivate und deren herstellung - Google Patents
Tetrahydronaphthalinderivate und deren herstellungInfo
- Publication number
- DE2340629A1 DE2340629A1 DE19732340629 DE2340629A DE2340629A1 DE 2340629 A1 DE2340629 A1 DE 2340629A1 DE 19732340629 DE19732340629 DE 19732340629 DE 2340629 A DE2340629 A DE 2340629A DE 2340629 A1 DE2340629 A1 DE 2340629A1
- Authority
- DE
- Germany
- Prior art keywords
- tetrahydronaphthalene
- formula
- compounds
- acid addition
- addition salts
- 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
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical class C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 title claims description 8
- 238000004519 manufacturing process Methods 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 31
- 238000000034 method Methods 0.000 claims description 21
- 239000002253 acid Substances 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 19
- -1 1,1-Diethyl-2-amino-7-methoxy-1, 2,3,4-tetrahydronaphthalene Chemical compound 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 3
- 125000004663 dialkyl amino group Chemical group 0.000 claims 2
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims 1
- 230000002152 alkylating effect Effects 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000000047 product Substances 0.000 description 11
- OROGSEYTTFOCAN-DNJOTXNNSA-N codeine Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC OROGSEYTTFOCAN-DNJOTXNNSA-N 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- 238000000921 elemental analysis Methods 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 230000000202 analgesic effect Effects 0.000 description 7
- 239000007795 chemical reaction product Substances 0.000 description 7
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 229960004126 codeine Drugs 0.000 description 5
- OROGSEYTTFOCAN-UHFFFAOYSA-N hydrocodone Natural products C1C(N(CCC234)C)C2C=CC(O)C3OC2=C4C1=CC=C2OC OROGSEYTTFOCAN-UHFFFAOYSA-N 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 238000006722 reduction reaction Methods 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 238000010520 demethylation reaction Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000005804 alkylation reaction Methods 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000017858 demethylation Effects 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 230000002829 reductive effect Effects 0.000 description 3
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 229940126062 Compound A Drugs 0.000 description 2
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- 238000007126 N-alkylation reaction Methods 0.000 description 2
- 239000007868 Raney catalyst Substances 0.000 description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- 230000007059 acute toxicity Effects 0.000 description 2
- 231100000403 acute toxicity Toxicity 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- 230000000638 stimulation Effects 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- PXPFLCAHCFHMJY-UHFFFAOYSA-N 7-amino-8,8-dipropyl-6,7-dihydro-5h-naphthalen-2-ol Chemical compound C1=C(O)C=C2C(CCC)(CCC)C(N)CCC2=C1 PXPFLCAHCFHMJY-UHFFFAOYSA-N 0.000 description 1
- XUEZQNCODZZZHP-UHFFFAOYSA-N 7-methoxy-1,1-dimethyl-3,4-dihydro-2h-naphthalen-2-amine Chemical compound C1CC(N)C(C)(C)C2=CC(OC)=CC=C21 XUEZQNCODZZZHP-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 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
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 241000978776 Senegalia senegal Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 238000004166 bioassay Methods 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 150000008050 dialkyl sulfates Chemical class 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- GGCJLWBMJYGIRE-UHFFFAOYSA-N ethanol;formaldehyde Chemical compound O=C.CCO GGCJLWBMJYGIRE-UHFFFAOYSA-N 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- PMKFMRWUBQUUPR-UHFFFAOYSA-N n-(1,1-diethyl-7-methoxy-3,4-dihydronaphthalen-2-ylidene)hydroxylamine Chemical compound C1=C(OC)C=C2C(CC)(CC)C(=NO)CCC2=C1 PMKFMRWUBQUUPR-UHFFFAOYSA-N 0.000 description 1
- WOSZXSLDXPEZKU-UHFFFAOYSA-N n-(7-methoxy-1,1-dimethyl-3,4-dihydronaphthalen-2-ylidene)hydroxylamine Chemical compound C1CC(=NO)C(C)(C)C2=CC(OC)=CC=C21 WOSZXSLDXPEZKU-UHFFFAOYSA-N 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000006485 reductive methylation reaction Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP47080724A JPS5124508B2 (enrdf_load_stackoverflow) | 1972-08-14 | 1972-08-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2340629A1 true DE2340629A1 (de) | 1974-03-21 |
Family
ID=13726296
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19732340629 Pending DE2340629A1 (de) | 1972-08-14 | 1973-08-10 | Tetrahydronaphthalinderivate und deren herstellung |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS5124508B2 (enrdf_load_stackoverflow) |
| CH (1) | CH589600A5 (enrdf_load_stackoverflow) |
| DE (1) | DE2340629A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2196158B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1377356A (enrdf_load_stackoverflow) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL65501A (en) * | 1981-05-08 | 1986-04-29 | Astra Laekemedel Ab | 1-alkyl-2-aminotetralin derivatives,process for their preparation and pharmaceutical compositions containing them |
| CA1331191C (en) | 1988-03-25 | 1994-08-02 | Bengt Ronny Andersson | Therapeutically useful tetralin derivatives |
| US5225596A (en) * | 1989-01-09 | 1993-07-06 | The Upjohn Company | Halo substituted aminotetralins |
| ES2123500T3 (es) * | 1989-05-31 | 1999-01-16 | Upjohn Co | Derivados de 8-heterociclil-2-aminotetralina activos sobre el sistema nervioso central. |
| US5486611A (en) * | 1989-07-13 | 1996-01-23 | The Upjohn Company | Carboxamido-(1,2N)-carbocyclic-2-aminotetralin derivatives |
| WO2000037426A1 (en) * | 1998-12-22 | 2000-06-29 | Astrazeneca Ab | Novel oxo-aminotetralin compounds useful in pain management |
| US6844368B1 (en) | 1998-12-22 | 2005-01-18 | Edward Roberts | Compounds useful in pain management |
| EP1140815A1 (en) * | 1998-12-22 | 2001-10-10 | AstraZeneca AB | Novel thio-aminotetralin compounds useful in pain management |
| US6498196B1 (en) | 1998-12-22 | 2002-12-24 | Edward Roberts | Compounds useful in pain management |
-
1972
- 1972-08-14 JP JP47080724A patent/JPS5124508B2/ja not_active Expired
-
1973
- 1973-08-09 CH CH1151473A patent/CH589600A5/xx not_active IP Right Cessation
- 1973-08-10 DE DE19732340629 patent/DE2340629A1/de active Pending
- 1973-08-13 FR FR7329545A patent/FR2196158B1/fr not_active Expired
- 1973-08-14 GB GB3838673A patent/GB1377356A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5124508B2 (enrdf_load_stackoverflow) | 1976-07-24 |
| GB1377356A (en) | 1974-12-11 |
| FR2196158A1 (enrdf_load_stackoverflow) | 1974-03-15 |
| FR2196158B1 (enrdf_load_stackoverflow) | 1976-12-31 |
| CH589600A5 (enrdf_load_stackoverflow) | 1977-07-15 |
| JPS4954353A (enrdf_load_stackoverflow) | 1974-05-27 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2345064C3 (de) | 4-Amino-2-<l,2r3,4-tetrahydroisochinolin-2 yl)-chinazolinderivate und diese enthaltende Arzneimittel | |
| EP0092814A1 (de) | Neue Zwischenprodukte zur Herstellung N-Alkylnorscopine, Verfahren zu ihrer Herstellung und ihre Verwendung | |
| DE2403138A1 (de) | Benzylaminderivate und verfahren zu ihrer herstellung | |
| DE2461604C2 (enrdf_load_stackoverflow) | ||
| DE1470125C3 (de) | 4-Oxo-13,8-triazaspiro [4,5] decane | |
| DE2340629A1 (de) | Tetrahydronaphthalinderivate und deren herstellung | |
| DE2420618A1 (de) | Aminoalkylanilide | |
| DE1795832C3 (de) | O-Aminoarylketimine und Verfahren zu ihrer Herstellung | |
| DE2413102A1 (de) | Verfahren zur herstellung von 1-(3,5dihydroxyphenyl)-1-hydroxy-2- eckige klammer auf 1-methyl-2-(4-hydroxyphenyl)-aethyl eckige klammer zu -amino-aethan | |
| DE1227447B (de) | Verfahren zur Herstellung von Phenylisopropylaminen | |
| DE1286047B (de) | Verfahren zur Herstellung von Diaralkylaminen und deren Saeureadditionssalzen | |
| CH615412A5 (enrdf_load_stackoverflow) | ||
| DE1802297C3 (de) | Isopropylaminderivate und Verfahren zu ihrer Herstellung | |
| DE2542791C2 (de) | N,N'-Disubstituierte Naphthylacetamidine | |
| DE1543388B1 (de) | Basisch substituierte,tricyclische heterocyclische Verbindungen und deren pharmakologisch nicht giftige Salze sowie Verfahren zu ihrer Herstellung | |
| DE2003744C2 (de) | In 3- und 4-Stellung disubstituierte 3-Amino-2-bicyclo[2,2,2]octan-2-ole, Verfahren zu deren Herstellung und dieselben enthaltende Arzneimittel | |
| DE69711654T2 (de) | Acridonderivate und verfahren zur herstellung von 8-hydroxyimidazoacridinonderivaten | |
| DE2849766A1 (de) | 6-nieder-alkyl-7,8-dihydroxy-1-phenyl-2,3,4,5-tetrahydro-1h-3-benzazepine sowie deren salze mit saeuren und ihre verwendung als dopaminerge wirkstoffe | |
| DE2357346A1 (de) | 3-alkylamino-4-hydroxy-alpha-aminomethylbenzylalkohole, ihre salze, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel | |
| EP0128437B1 (de) | Neues Nortropinderivat, Verfahren zu seiner Herstellung und seine Verwendung | |
| DE2159678C3 (de) | Boranoazepine und Verfahren zur Herstellung von Amino-10,11-dihydro- dibenzo [b,f] azepinen | |
| DE2354327B2 (de) | 2-amino-1,2,3,4-tetrahydronaphthalin- derivate, verfahren zu deren herstellung und verfahren zur herstellung von 6,7- benzomorphanen ausgehend von jenen | |
| DE1518652A1 (de) | Verfahren zur Herstellung von pharmazeutisch wirksamen Derivaten des 2-Aminoindans | |
| AT338793B (de) | Verfahren zur herstellung von neuen benzazocinderivaten | |
| AT376659B (de) | Verfahren zur herstellung von neuen substituierten 2-benzylpyrrolidinen |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHA | Expiration of time for request for examination |