CH544764A - Verfahren zur Herstellung von neuen Triazolo-benzodiazepinderivaten - Google Patents
Verfahren zur Herstellung von neuen Triazolo-benzodiazepinderivatenInfo
- Publication number
- CH544764A CH544764A CH1206173A CH1206173A CH544764A CH 544764 A CH544764 A CH 544764A CH 1206173 A CH1206173 A CH 1206173A CH 1206173 A CH1206173 A CH 1206173A CH 544764 A CH544764 A CH 544764A
- Authority
- CH
- Switzerland
- Prior art keywords
- carbon atoms
- alkyl
- group
- hydrolysis
- general formula
- Prior art date
Links
- 239000003874 central nervous system depressant Substances 0.000 title abstract 2
- 229940049706 benzodiazepine Drugs 0.000 title description 4
- 230000000694 effects Effects 0.000 title description 2
- 150000003839 salts Chemical class 0.000 claims abstract description 15
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 9
- 230000007062 hydrolysis Effects 0.000 claims abstract description 7
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 7
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 6
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 7
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 7
- 150000007522 mineralic acids Chemical class 0.000 claims description 7
- 150000007524 organic acids Chemical class 0.000 claims description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 5
- 229940093915 gynecological organic acid Drugs 0.000 claims description 5
- 235000005985 organic acids Nutrition 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 229960000583 acetic acid Drugs 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 229910000042 hydrogen bromide Inorganic materials 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- KYTREVLPRJOBEM-UHFFFAOYSA-N triazolo[4,5-i][1,2]benzodiazepine Chemical class C1=CC2=CC=CN=NC2=C2C1=NN=N2 KYTREVLPRJOBEM-UHFFFAOYSA-N 0.000 claims description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 239000012458 free base Substances 0.000 claims description 2
- 239000012362 glacial acetic acid Substances 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 230000001419 dependent effect Effects 0.000 claims 2
- -1 polymethyleneimino Polymers 0.000 abstract description 18
- 239000002253 acid Substances 0.000 abstract description 5
- 238000006243 chemical reaction Methods 0.000 abstract description 5
- 125000002252 acyl group Chemical group 0.000 abstract description 2
- 125000004414 alkyl thio group Chemical group 0.000 abstract description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract description 2
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 abstract 1
- 125000005544 phthalimido group Chemical group 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 239000002585 base Substances 0.000 description 4
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 4
- GUJAGMICFDYKNR-UHFFFAOYSA-N 1,4-benzodiazepine Chemical compound N1C=CN=CC2=CC=CC=C12 GUJAGMICFDYKNR-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- YOHJKBKLWJAEHF-UHFFFAOYSA-N 7-chloro-2-methylsulfanyl-5-phenyl-3h-1,4-benzodiazepine Chemical compound N=1CC(SC)=NC2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 YOHJKBKLWJAEHF-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 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
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- ZMJBYMUCKBYSCP-UHFFFAOYSA-N (+)-Erythro-hydroxycitric acid Natural products OC(=O)C(O)C(O)(C(O)=O)CC(O)=O ZMJBYMUCKBYSCP-UHFFFAOYSA-N 0.000 description 1
- 125000005919 1,2,2-trimethylpropyl group Chemical group 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-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
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- LZANARFQFSEWHV-UHFFFAOYSA-N 5-phenyl-1,3-dihydro-1,4-benzodiazepine-2-thione Chemical class C12=CC=CC=C2NC(=S)CN=C1C1=CC=CC=C1 LZANARFQFSEWHV-UHFFFAOYSA-N 0.000 description 1
- FPZAMNOXVVYEPG-UHFFFAOYSA-N 7-chloro-2-methyl-5-phenyl-3H-1,4-benzodiazepin-3-amine Chemical compound CC1=NC2=C(C(=NC1N)C1=CC=CC=C1)C=C(C=C2)Cl FPZAMNOXVVYEPG-UHFFFAOYSA-N 0.000 description 1
- CJAYKFPAEBBMQF-UHFFFAOYSA-N 7-chloro-5-(2-chlorophenyl)-2-methylsulfanyl-3h-1,4-benzodiazepine Chemical compound N=1CC(SC)=NC2=CC=C(Cl)C=C2C=1C1=CC=CC=C1Cl CJAYKFPAEBBMQF-UHFFFAOYSA-N 0.000 description 1
- 208000019901 Anxiety disease Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 206010052904 Musculoskeletal stiffness Diseases 0.000 description 1
- CJUMAFVKTCBCJK-UHFFFAOYSA-N N-benzyloxycarbonylglycine Chemical compound OC(=O)CNC(=O)OCC1=CC=CC=C1 CJUMAFVKTCBCJK-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 150000001346 alkyl aryl ethers Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 230000002539 anti-aggressive effect Effects 0.000 description 1
- 230000002082 anti-convulsion Effects 0.000 description 1
- 230000036506 anxiety Effects 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- HDFRDWFLWVCOGP-UHFFFAOYSA-N carbonothioic O,S-acid Chemical compound OC(S)=O HDFRDWFLWVCOGP-UHFFFAOYSA-N 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 229940019778 diethylene glycol diethyl ether Drugs 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 206010015037 epilepsy Diseases 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 1
- XTLNYNMNUCLWEZ-UHFFFAOYSA-N ethanol;propan-2-one Chemical compound CCO.CC(C)=O XTLNYNMNUCLWEZ-UHFFFAOYSA-N 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-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
- 238000001914 filtration Methods 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 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
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000006678 phenoxycarbonyl group Chemical group 0.000 description 1
- 239000000047 product 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
- 230000035484 reaction time Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1206173A CH544764A (de) | 1971-01-21 | 1971-01-21 | Verfahren zur Herstellung von neuen Triazolo-benzodiazepinderivaten |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH89171 | 1971-01-21 | ||
| CH1206173A CH544764A (de) | 1971-01-21 | 1971-01-21 | Verfahren zur Herstellung von neuen Triazolo-benzodiazepinderivaten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH544764A true CH544764A (de) | 1974-01-15 |
Family
ID=4197579
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1206173A CH544764A (de) | 1971-01-21 | 1971-01-21 | Verfahren zur Herstellung von neuen Triazolo-benzodiazepinderivaten |
| CH89171A CH545803A (pl) | 1971-01-21 | 1971-01-21 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH89171A CH545803A (pl) | 1971-01-21 | 1971-01-21 |
Country Status (19)
| Country | Link |
|---|---|
| AR (1) | AR192612A1 (pl) |
| AT (3) | AT315862B (pl) |
| AU (1) | AU475348B2 (pl) |
| BE (1) | BE778215A (pl) |
| CA (1) | CA965786A (pl) |
| CH (2) | CH544764A (pl) |
| CS (2) | CS185640B2 (pl) |
| DD (1) | DD95010A5 (pl) |
| DE (1) | DE2201210A1 (pl) |
| ES (1) | ES399064A1 (pl) |
| FR (1) | FR2122485B1 (pl) |
| GB (2) | GB1394568A (pl) |
| HU (1) | HU166550B (pl) |
| IE (1) | IE35968B1 (pl) |
| IL (1) | IL38553A (pl) |
| NL (1) | NL7200538A (pl) |
| PL (2) | PL86933B1 (pl) |
| SU (1) | SU481156A3 (pl) |
| ZA (1) | ZA72253B (pl) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2709842A1 (de) * | 1976-03-15 | 1977-09-22 | Upjohn Co | Benzodiazepine, verfahren zu ihrer herstellung und diese enthaltende arzneimittel |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1381158A (en) * | 1971-09-13 | 1975-01-22 | Upjohn Co | Benzodiazepines and the manufacture thereof |
| US3767661A (en) * | 1971-09-13 | 1973-10-23 | Upjohn Co | 4h-s-triazolo(4,3-a)(1,4)benzodiazepines |
| US3767660A (en) * | 1971-09-13 | 1973-10-23 | Upjohn Co | 4h-s-triazolo(4,3-a)(1,4)benzodiazepines |
| BE790838A (fr) * | 1971-11-02 | 1973-04-30 | Upjohn Co | Nouvelles 1-aminophenyl-6-phenyl-s-triazolo (4,3-a) (1,4)- benzodiazepines, leur procede de preparation et medicament les contenant |
| DE2356369C2 (de) * | 1972-11-24 | 1984-08-23 | The Upjohn Co., Kalamazoo, Mich. | Pharmazeutisches Präparat, enthaltend eine oder mehrere Benzodiazepinverbindungen |
| US3842090A (en) * | 1973-02-14 | 1974-10-15 | Upjohn Co | Certain 1-aminomethyl-6-phenyl 4h-s-triazolo(4,3-a)(1,4)benzodiazepines |
| US4501698A (en) * | 1983-03-31 | 1985-02-26 | The Upjohn Company | Preparing 1-(hydroxymethyl)-triazolobenzodiazepines and 1-(aminomethyl)-triazolobenzodiazepines |
| CA1234810A (en) * | 1983-12-19 | 1988-04-05 | Steve Nichols | Non-hygroscopic adinazolam methanesulfonate salt and process therefor |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3987052A (en) * | 1969-03-17 | 1976-10-19 | The Upjohn Company | 6-Phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepines |
-
1971
- 1971-01-21 CH CH1206173A patent/CH544764A/de not_active IP Right Cessation
- 1971-01-21 CH CH89171A patent/CH545803A/xx not_active IP Right Cessation
-
1972
- 1972-01-11 IE IE38/72A patent/IE35968B1/xx unknown
- 1972-01-12 CA CA132,223A patent/CA965786A/en not_active Expired
- 1972-01-12 DE DE19722201210 patent/DE2201210A1/de active Pending
- 1972-01-13 IL IL38553A patent/IL38553A/xx unknown
- 1972-01-13 NL NL7200538A patent/NL7200538A/xx not_active Application Discontinuation
- 1972-01-14 GB GB4320574A patent/GB1394568A/en not_active Expired
- 1972-01-14 GB GB184472A patent/GB1393256A/en not_active Expired
- 1972-01-14 ZA ZA720253A patent/ZA72253B/xx unknown
- 1972-01-18 FR FR7201534A patent/FR2122485B1/fr not_active Expired
- 1972-01-19 AU AU38047/72A patent/AU475348B2/en not_active Expired
- 1972-01-19 BE BE778215A patent/BE778215A/xx unknown
- 1972-01-19 HU HUCI1202A patent/HU166550B/hu unknown
- 1972-01-19 SU SU1959120A patent/SU481156A3/ru active
- 1972-01-20 PL PL1972175725A patent/PL86933B1/pl unknown
- 1972-01-20 AT AT501873A patent/AT315862B/de not_active IP Right Cessation
- 1972-01-20 AT AT501973A patent/AT315863B/de not_active IP Right Cessation
- 1972-01-20 PL PL1972153001A patent/PL83109B1/pl unknown
- 1972-01-20 AT AT46372A patent/AT315848B/de not_active IP Right Cessation
- 1972-01-20 CS CS7500008670A patent/CS185640B2/cs unknown
- 1972-01-20 CS CS7200000387A patent/CS185604B2/cs unknown
- 1972-01-20 DD DD160445A patent/DD95010A5/xx unknown
- 1972-01-20 ES ES399064A patent/ES399064A1/es not_active Expired
- 1972-01-21 AR AR240178A patent/AR192612A1/es active
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2709842A1 (de) * | 1976-03-15 | 1977-09-22 | Upjohn Co | Benzodiazepine, verfahren zu ihrer herstellung und diese enthaltende arzneimittel |
Also Published As
| Publication number | Publication date |
|---|---|
| IE35968B1 (en) | 1976-07-07 |
| AU475348B2 (en) | 1976-08-19 |
| SU444370A3 (ru) | 1974-09-25 |
| FR2122485B1 (pl) | 1975-02-07 |
| SU481156A3 (ru) | 1975-08-15 |
| HU166550B (pl) | 1975-04-28 |
| CA965786A (en) | 1975-04-08 |
| IE35968L (en) | 1972-07-21 |
| ES399064A1 (es) | 1975-06-01 |
| PL83109B1 (en) | 1975-12-31 |
| NL7200538A (pl) | 1972-07-25 |
| AR192612A1 (es) | 1973-02-28 |
| ZA72253B (en) | 1972-09-27 |
| FR2122485A1 (pl) | 1972-09-01 |
| GB1394568A (en) | 1975-05-21 |
| BE778215A (fr) | 1972-07-19 |
| IL38553A (en) | 1975-02-10 |
| CH545803A (pl) | 1974-02-15 |
| AT315862B (de) | 1974-06-10 |
| AT315848B (de) | 1974-06-10 |
| GB1393256A (en) | 1975-05-07 |
| AT315863B (de) | 1974-06-10 |
| PL86933B1 (en) | 1976-06-30 |
| IL38553A0 (en) | 1972-03-28 |
| DD95010A5 (pl) | 1973-01-12 |
| CS185640B2 (en) | 1978-10-31 |
| CS185604B2 (en) | 1978-10-31 |
| DE2201210A1 (de) | 1972-08-03 |
| AU3804772A (en) | 1973-07-26 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE69128236T2 (de) | N-Acyl-2,3-benzodiazepin-Derivate, diese enthaltende pharmazeutische Zusammensetzungen und Verfahren zu ihrer Herstellung | |
| DE1810423A1 (de) | 1-Phenyl-4-alkyl-3H-1,4-benzodiazepin-2,5-[1H,4H]-dione und Verfahren zu ihrer Herstellung | |
| DE2508045A1 (de) | Substituierte n-(1-benzylpyrrolidinyl-2-alkyl)-benzamide, verfahren zu deren herstellung und diese enthaltende arzneimittel | |
| CH544764A (de) | Verfahren zur Herstellung von neuen Triazolo-benzodiazepinderivaten | |
| US3933802A (en) | New sulphamoylbenzoic acid amides | |
| US3778504A (en) | Certain benzimidazoles used as antiinflammatory agents | |
| US3121074A (en) | Nitro substituted jh-l | |
| US3320247A (en) | Phenthiazine compounds | |
| DE2223681A1 (de) | Neue heterocyclische Verbindungen und Verfahren zu ihrer Herstellung | |
| DE2353187A1 (de) | Neue benzodiazepinderivate | |
| CH558803A (de) | Verfahren zur herstellung von neuen triazolo-benzodiazepinderivaten. | |
| DE69319945T2 (de) | 1,5-Benzodiazepinderivate und deren Verwendung in Heilmittel | |
| DE2855853C2 (de) | N-(1-Benzyl-2-methyl-3-pyrrolidinyl)-5-chlor-2-methoxy-4-methylaminobenzamid dessen Säureadditionssalze, Verfahren zu deren Herstellung und ihre Verwendung | |
| US3329701A (en) | Cyanobenzophenones | |
| DE1695092B2 (de) | N-(4-Sulfonamidophenyl)-a-alkylsuccinimide und deren Salze mit Basen, Verfahren zu ihrer Herstellung und pharmazeutische Zusammensetzungen | |
| US3300481A (en) | Process for the preparation of 5-thienyl-1, 3-dihydro-2h-1, 4-benzodiazepin-2-one-4-oxides | |
| AT265289B (de) | Verfahren zur Herstellung von neuen Azepinderivaten sowie von ihren Additionssalzen mit anorganischen oder organischen Säuren | |
| AT330786B (de) | Verfahren zur herstellung von neuen diazepinderivaten | |
| AT344183B (de) | Verfahren zur herstellung von neuen thienotriazolodiazepin-derivaten und ihren saeureadditionssalzen | |
| AT330787B (de) | Verfahren zur herstellung von neuen diazepinderivaten und deren salzen | |
| DE2609764A1 (de) | Acetamidoxime, verfahren zu ihrer herstellung und sie enthaltendes arzneimittel | |
| CH567024A5 (en) | 1-Aminoalkyl-triazolo(4,3-a) (1,4) benzodiazepines - CNS depressants prepd. from corresp 1-phthalimidoalkyl cpds by treatment with hydrazine or acid | |
| AT312615B (de) | Verfahren zur Herstellung von neuen 2(1H)-Chinazolinonen | |
| AT262290B (de) | Verfahren zur Herstellung von neuen Acridanderivaten und ihren Additionssalzen mit anorganischen und organischen Säuren | |
| DE2118262C3 (de) | 1,5-Benzodtazepinphosphorverbindungen, Verfahren zu ihrer Herstellung und diese enthaltende Mittel |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |