DE2361201A1 - Neue n-n'-disubstituierte amidine und saeureadditionssalze dieser - Google Patents
Neue n-n'-disubstituierte amidine und saeureadditionssalze dieserInfo
- Publication number
- DE2361201A1 DE2361201A1 DE19732361201 DE2361201A DE2361201A1 DE 2361201 A1 DE2361201 A1 DE 2361201A1 DE 19732361201 DE19732361201 DE 19732361201 DE 2361201 A DE2361201 A DE 2361201A DE 2361201 A1 DE2361201 A1 DE 2361201A1
- Authority
- DE
- Germany
- Prior art keywords
- cyclohexyl
- hydrochloride
- toluamidine
- tolyl
- benzamidine
- 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
- 150000001409 amidines Chemical class 0.000 title claims description 9
- 239000002253 acid Chemical class 0.000 title claims description 7
- -1 ethylphenyl Chemical group 0.000 claims description 73
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 42
- 239000000126 substance Substances 0.000 claims description 14
- 150000003254 radicals Chemical class 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical compound [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 claims description 4
- 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 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- USHZYUPZIKQYMI-UHFFFAOYSA-N 2-methylbenzenecarboximidamide;hydrochloride Chemical compound Cl.CC1=CC=CC=C1C(N)=N USHZYUPZIKQYMI-UHFFFAOYSA-N 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 230000000954 anitussive effect Effects 0.000 description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 150000001412 amines Chemical class 0.000 description 9
- 238000001816 cooling Methods 0.000 description 8
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 229940124584 antitussives Drugs 0.000 description 6
- DKSZLDSPXIWGFO-BLOJGBSASA-N (4r,4ar,7s,7ar,12bs)-9-methoxy-3-methyl-2,4,4a,7,7a,13-hexahydro-1h-4,12-methanobenzofuro[3,2-e]isoquinoline-7-ol;phosphoric acid;hydrate Chemical compound O.OP(O)(O)=O.OP(O)(O)=O.C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC.C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC DKSZLDSPXIWGFO-BLOJGBSASA-N 0.000 description 5
- 239000003434 antitussive agent Substances 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 229960004415 codeine phosphate Drugs 0.000 description 5
- 239000012452 mother liquor Substances 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 239000003208 petroleum Substances 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- HRXZRAXKKNUKRF-UHFFFAOYSA-N 4-ethylaniline Chemical compound CCC1=CC=C(N)C=C1 HRXZRAXKKNUKRF-UHFFFAOYSA-N 0.000 description 4
- 230000007059 acute toxicity Effects 0.000 description 4
- 231100000403 acute toxicity Toxicity 0.000 description 4
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 4
- 125000001841 imino group Chemical group [H]N=* 0.000 description 4
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 4
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- JJYPMNFTHPTTDI-UHFFFAOYSA-N meta-toluidine Natural products CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- AKNNEGZIBPJZJG-MSOLQXFVSA-N (-)-noscapine Chemical compound CN1CCC2=CC=3OCOC=3C(OC)=C2[C@@H]1[C@@H]1C2=CC=C(OC)C(OC)=C2C(=O)O1 AKNNEGZIBPJZJG-MSOLQXFVSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- FLNXBVJLPJNOSI-UHFFFAOYSA-N 1-[2-[(4-chlorophenyl)-phenylmethoxy]ethyl]piperidine Chemical compound C1=CC(Cl)=CC=C1C(C=1C=CC=CC=1)OCCN1CCCCC1 FLNXBVJLPJNOSI-UHFFFAOYSA-N 0.000 description 2
- DOLQYFPDPKPQSS-UHFFFAOYSA-N 3,4-dimethylaniline Chemical group CC1=CC=C(N)C=C1C DOLQYFPDPKPQSS-UHFFFAOYSA-N 0.000 description 2
- JGLMVXWAHNTPRF-CMDGGOBGSA-N CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O Chemical compound CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O JGLMVXWAHNTPRF-CMDGGOBGSA-N 0.000 description 2
- AKJDEXBCRLOVTH-UHFFFAOYSA-N Carbetapentane citrate Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O.C=1C=CC=CC=1C1(C(=O)OCCOCCN(CC)CC)CCCC1 AKJDEXBCRLOVTH-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methyl-N-phenylamine Natural products CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 2
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 2
- 150000007514 bases Chemical class 0.000 description 2
- 229940098391 carbetapentane citrate Drugs 0.000 description 2
- 229960002544 cloperastine Drugs 0.000 description 2
- 238000004042 decolorization Methods 0.000 description 2
- JSYGRUBHOCKMGQ-UHFFFAOYSA-N dichloramine Chemical compound ClNCl JSYGRUBHOCKMGQ-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- NCBZRJODKRCREW-UHFFFAOYSA-N m-anisidine Chemical compound COC1=CC=CC(N)=C1 NCBZRJODKRCREW-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 238000003419 tautomerization reaction Methods 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- 125000003944 tolyl group Chemical group 0.000 description 2
- YQSHYGCCYVPRDI-UHFFFAOYSA-N (4-propan-2-ylphenyl)methanamine Chemical compound CC(C)C1=CC=C(CN)C=C1 YQSHYGCCYVPRDI-UHFFFAOYSA-N 0.000 description 1
- WPWHSFAFEBZWBB-UHFFFAOYSA-N 1-butyl radical Chemical compound [CH2]CCC WPWHSFAFEBZWBB-UHFFFAOYSA-N 0.000 description 1
- VVAKEQGKZNKUSU-UHFFFAOYSA-N 2,3-dimethylaniline Chemical group CC1=CC=CC(N)=C1C VVAKEQGKZNKUSU-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- DUSYVXRZSXLXRH-UHFFFAOYSA-N 3-methyl-n-phenylbenzamide Chemical compound CC1=CC=CC(C(=O)NC=2C=CC=CC=2)=C1 DUSYVXRZSXLXRH-UHFFFAOYSA-N 0.000 description 1
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 206010052804 Drug tolerance Diseases 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-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
- 241001465754 Metazoa Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- PLJBJADAJAPYRD-UHFFFAOYSA-N N'-cyclohexyl-3-methyl-N-(3-methylphenyl)benzenecarboximidamide Chemical compound CC1=CC=CC(N=C(NC2CCCCC2)C=2C=C(C)C=CC=2)=C1 PLJBJADAJAPYRD-UHFFFAOYSA-N 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- 241000784303 Ochrosia compta Species 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229960003782 dextromethorphan hydrobromide Drugs 0.000 description 1
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical compound C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 230000026781 habituation Effects 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- MSVZUEGLXXVUJS-UHFFFAOYSA-N hydron;n-(2-piperidin-1-ylethyl)-n-(pyridin-2-ylmethyl)aniline;chloride Chemical compound Cl.C=1C=CC=NC=1CN(C=1C=CC=CC=1)CCN1CCCCC1 MSVZUEGLXXVUJS-UHFFFAOYSA-N 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- FNEAZWBKUPLXSO-UHFFFAOYSA-N n'-cyclohexylbenzenecarboximidamide Chemical compound C=1C=CC=CC=1C(=N)NC1CCCCC1 FNEAZWBKUPLXSO-UHFFFAOYSA-N 0.000 description 1
- UCAIXIMMSIJHND-UHFFFAOYSA-N n-(3,4-dimethylphenyl)benzamide Chemical compound C1=C(C)C(C)=CC=C1NC(=O)C1=CC=CC=C1 UCAIXIMMSIJHND-UHFFFAOYSA-N 0.000 description 1
- MDXWMUYRRDYWKZ-UHFFFAOYSA-N n-cyclohexyl-2-methylbenzamide Chemical compound CC1=CC=CC=C1C(=O)NC1CCCCC1 MDXWMUYRRDYWKZ-UHFFFAOYSA-N 0.000 description 1
- FNTGEXAHADFYNU-UHFFFAOYSA-N n-cyclohexyl-3-methylbenzamide Chemical compound CC1=CC=CC(C(=O)NC2CCCCC2)=C1 FNTGEXAHADFYNU-UHFFFAOYSA-N 0.000 description 1
- XMKXRGAYXMSAAW-UHFFFAOYSA-N n-cyclohexyl-4-methylbenzamide Chemical compound C1=CC(C)=CC=C1C(=O)NC1CCCCC1 XMKXRGAYXMSAAW-UHFFFAOYSA-N 0.000 description 1
- KQJYDHWNYPRIRY-UHFFFAOYSA-N n-cyclohexylbenzamide Chemical compound C=1C=CC=CC=1C(=O)NC1CCCCC1 KQJYDHWNYPRIRY-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 1
- 239000003348 petrochemical agent Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP47122773A JPS4976837A (OSRAM) | 1972-12-06 | 1972-12-06 | |
| JP12277472A JPS4985036A (OSRAM) | 1972-12-06 | 1972-12-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2361201A1 true DE2361201A1 (de) | 1974-06-20 |
Family
ID=26459825
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19732361201 Pending DE2361201A1 (de) | 1972-12-06 | 1973-12-06 | Neue n-n'-disubstituierte amidine und saeureadditionssalze dieser |
Country Status (5)
| Country | Link |
|---|---|
| CH (1) | CH578517A5 (OSRAM) |
| DE (1) | DE2361201A1 (OSRAM) |
| FR (1) | FR2209572B1 (OSRAM) |
| GB (1) | GB1394299A (OSRAM) |
| HU (1) | HU167391B (OSRAM) |
-
1973
- 1973-12-05 CH CH1702473A patent/CH578517A5/xx not_active IP Right Cessation
- 1973-12-06 GB GB5647873A patent/GB1394299A/en not_active Expired
- 1973-12-06 FR FR7343585A patent/FR2209572B1/fr not_active Expired
- 1973-12-06 HU HUTO000945 patent/HU167391B/hu unknown
- 1973-12-06 DE DE19732361201 patent/DE2361201A1/de active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| CH578517A5 (OSRAM) | 1976-08-13 |
| HU167391B (OSRAM) | 1975-09-27 |
| FR2209572A1 (OSRAM) | 1974-07-05 |
| FR2209572B1 (OSRAM) | 1976-09-03 |
| GB1394299A (en) | 1975-05-14 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE965036C (de) | Verfahren zur Herstellung von p-(Bis-2-chloraethyl-amino)-ª-phenyl-alanin | |
| DE1670536B2 (de) | Neue 2-Anilino-5-acylamino-pyrimidlne | |
| DE1906527C3 (de) | Thioninderivate, Verfahren zu deren Herstellung und pharmazeutische Präparate, welche diese enthalten | |
| CH380734A (de) | Verfahren zur Herstellung von neuen s-Triazinderivaten | |
| DE2535930A1 (de) | Abietamidderivate und verfahren zu ihrer herstellung | |
| DE2361201A1 (de) | Neue n-n'-disubstituierte amidine und saeureadditionssalze dieser | |
| DE1645974A1 (de) | Isonicotinsaeureamide enthaltende Arzneimittel | |
| DE2106705A1 (de) | Esterderivate von Tetrahydrocanna binolen | |
| DE2629756C2 (OSRAM) | ||
| DE1235929B (de) | Verfahren zur Herstellung von 2-(2'-Pyrazinyl)-benzimidazol und seinen Salzen | |
| DE2327193C3 (de) | N-(Diethylaminoethyl)-2-methoxy-5methylsulfonylbenzamid, seine Salze, Verfahren zur Herstellung dieser Verbindungen sowie diese Verbindungen enthaltende Arzneimittel | |
| AT226731B (de) | Verfahren zur Herstellung von neuen Guanidinverbindungen | |
| DE1595875C (de) | Phenothiazine und Verfahren zu deren Herstellung | |
| AT212470B (de) | Verfahren zur Herstellung von neuen Oxydationsfarbstoffen | |
| DE944854C (de) | Verfahren zur Herstellung von halogenierten 8-Oxychinolinverbindungen | |
| DE1801305A1 (de) | Verfahren zur Herstellung von 7-Chlor-2,3-dihydro-1-methyl-5-o-trifluormethylphenyl-1 H-1,4-benzodiazepin | |
| AT319960B (de) | Verfahren zur Herstellung von neuen Pyridazinverbindungen | |
| DE1795511C3 (de) | 3-Amino-5-phenyl-7-chlor-2,3dihydro-1 H-1,4-benzodiazepinon-(2) | |
| AT201584B (de) | Verfahren zur Herstellung neuer Anilide und deren Salze | |
| AT360007B (de) | Verfahren zur herstellung von 2-(phenylamino)- imidazolin-(2)derivaten und deren salzen | |
| DE895291C (de) | Verfahren zur Herstellung von Diazoamino-Derivaten | |
| AT222120B (de) | Verfahren zur Herstellung von neuen Tetrahydroisochinolin-Derivaten | |
| AT255426B (de) | Verfahren zur Herstellung von neuen Triazinen | |
| AT337199B (de) | Verfahren zur herstellung von neuen, tricyclischen kondensierten imidazol-derivaten | |
| AT210883B (de) | Verfahren zur Herstellung von neune substituierten Aminoacetophenonen und deren Salzen |