FI57258C - Foerfarande foer framstaellning av 1,3-dihydro-5-pyridyl-2h-1,4-bensodiazepin-derivat - Google Patents
Foerfarande foer framstaellning av 1,3-dihydro-5-pyridyl-2h-1,4-bensodiazepin-derivat Download PDFInfo
- Publication number
- FI57258C FI57258C FI1932/72A FI193272A FI57258C FI 57258 C FI57258 C FI 57258C FI 1932/72 A FI1932/72 A FI 1932/72A FI 193272 A FI193272 A FI 193272A FI 57258 C FI57258 C FI 57258C
- Authority
- FI
- Finland
- Prior art keywords
- dihydro
- pyridyl
- pyridine
- acid
- benzodiazepin
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 14
- RSAMJJNMSRCABO-UHFFFAOYSA-N 5-pyridin-2-yl-2,3-dihydro-1h-1,4-benzodiazepine Chemical class C12=CC=CC=C2NCCN=C1C1=CC=CC=N1 RSAMJJNMSRCABO-UHFFFAOYSA-N 0.000 title 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 48
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 claims description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 21
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 14
- 238000010992 reflux Methods 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 239000004312 hexamethylene tetramine Substances 0.000 claims description 12
- 235000010299 hexamethylene tetramine Nutrition 0.000 claims description 12
- 230000002378 acidificating effect Effects 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 239000003125 aqueous solvent Substances 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- VSTAQOGZTCSNAI-UHFFFAOYSA-N C1CNC2=CC=CC=C2C(=C1)C3=CC=CC=N3 Chemical class C1CNC2=CC=CC=C2C(=C1)C3=CC=CC=N3 VSTAQOGZTCSNAI-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
- 150000003222 pyridines Chemical class 0.000 claims description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- 229910021529 ammonia Inorganic materials 0.000 description 6
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- LYISZEZBKBGONS-UHFFFAOYSA-N n-[4-bromo-2-(pyridine-2-carbonyl)phenyl]-2-chloroacetamide Chemical compound ClCC(=O)NC1=CC=C(Br)C=C1C(=O)C1=CC=CC=N1 LYISZEZBKBGONS-UHFFFAOYSA-N 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- KHVZPFKJBLTYCC-UHFFFAOYSA-N (2-amino-5-bromophenyl)-pyridin-2-ylmethanone Chemical compound NC1=CC=C(Br)C=C1C(=O)C1=CC=CC=N1 KHVZPFKJBLTYCC-UHFFFAOYSA-N 0.000 description 3
- LSTRKXWIZZZYAS-UHFFFAOYSA-N 2-bromoacetyl bromide Chemical compound BrCC(Br)=O LSTRKXWIZZZYAS-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 230000001590 oxidative effect Effects 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- UVLXUZHEDUOEQB-UHFFFAOYSA-N 2-bromo-n-[4-bromo-2-(pyridine-2-carbonyl)phenyl]acetamide Chemical compound BrCC(=O)NC1=CC=C(Br)C=C1C(=O)C1=CC=CC=N1 UVLXUZHEDUOEQB-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- LTOIFRDKXOSNAX-UHFFFAOYSA-N 7-bromo-5-pyridin-2-yl-1,3-dihydro-1-benzazepin-2-one Chemical compound C12=CC(Br)=CC=C2NC(=O)CC=C1C1=CC=CC=N1 LTOIFRDKXOSNAX-UHFFFAOYSA-N 0.000 description 2
- OIKJAKIJCHBTGO-UHFFFAOYSA-N 7-chloro-1-methyl-5-phenyl-3H-1-benzazepin-2-one Chemical compound CN1c2ccc(Cl)cc2C(=CCC1=O)c1ccccc1 OIKJAKIJCHBTGO-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- WEWXXYDHYCDEKY-UHFFFAOYSA-N (2-aminophenyl)-pyridin-2-ylmethanone Chemical class NC1=CC=CC=C1C(=O)C1=CC=CC=N1 WEWXXYDHYCDEKY-UHFFFAOYSA-N 0.000 description 1
- RGGLEJFUEMKQSH-UHFFFAOYSA-N 1,4-benzodiazepin-2-one Chemical compound O=C1C=NC=C2C=CC=CC2=N1 RGGLEJFUEMKQSH-UHFFFAOYSA-N 0.000 description 1
- WFZFXUZFKAOTRR-UHFFFAOYSA-N 2,6-dimethyl-5-hepten-1-ol Chemical compound OCC(C)CCC=C(C)C WFZFXUZFKAOTRR-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- QMKXTRZCBCTUGO-UHFFFAOYSA-N 2-bromo-N-[4-chloro-2-(pyridine-2-carbonyl)phenyl]acetamide Chemical compound N1=C(C=CC=C1)C(=O)C1=C(C=CC(=C1)Cl)NC(CBr)=O QMKXTRZCBCTUGO-UHFFFAOYSA-N 0.000 description 1
- KCXOQEXVKIMZKB-UHFFFAOYSA-N 2-bromo-n-[2-(pyridine-2-carbonyl)phenyl]acetamide Chemical compound BrCC(=O)NC1=CC=CC=C1C(=O)C1=CC=CC=N1 KCXOQEXVKIMZKB-UHFFFAOYSA-N 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
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- FYNDMLHRRXAEKB-UHFFFAOYSA-N Br.BrCC(=O)NC1=C(C(=O)C2=NC=CC=C2)C=C(C=C1)Br Chemical compound Br.BrCC(=O)NC1=C(C(=O)C2=NC=CC=C2)C=C(C=C1)Br FYNDMLHRRXAEKB-UHFFFAOYSA-N 0.000 description 1
- VMIYHDSEFNYJSL-UHFFFAOYSA-N Bromazepam Chemical compound C12=CC(Br)=CC=C2NC(=O)CN=C1C1=CC=CC=N1 VMIYHDSEFNYJSL-UHFFFAOYSA-N 0.000 description 1
- AENNWQQBLAAMSP-UHFFFAOYSA-N C1=CC=NC(=C1)CC2=C(C=CC(=C2)Br)NC(=O)CCl Chemical compound C1=CC=NC(=C1)CC2=C(C=CC(=C2)Br)NC(=O)CCl AENNWQQBLAAMSP-UHFFFAOYSA-N 0.000 description 1
- FSHWKCQAZRXEHB-UHFFFAOYSA-N C1C=C(C2=CC=CC=C2NC1=O)C3=CC=CC=N3 Chemical compound C1C=C(C2=CC=CC=C2NC1=O)C3=CC=CC=N3 FSHWKCQAZRXEHB-UHFFFAOYSA-N 0.000 description 1
- WKADVEZWZGFSTE-UHFFFAOYSA-N C1CNC2=C(C=C(C=C2)Br)C(=C1)C3=CC=CC=N3 Chemical compound C1CNC2=C(C=C(C=C2)Br)C(=C1)C3=CC=CC=N3 WKADVEZWZGFSTE-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
- 206010049816 Muscle tightness Diseases 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- 230000001773 anti-convulsant effect Effects 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 229940106681 chloroacetic acid Drugs 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- -1 haloacetyl halide Chemical class 0.000 description 1
- 239000011874 heated mixture Substances 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- NGDSBQHTMKGUQU-UHFFFAOYSA-N methenamine hydrochloride Chemical compound Cl.C([N@@](C1)C2)[N@]3C[N@@]2C[N@@]1C3 NGDSBQHTMKGUQU-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000005057 refrigeration Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
- C07D213/46—Oxygen atoms
- C07D213/50—Ketonic radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3210771 | 1971-07-08 | ||
| GB3210771A GB1383647A (en) | 1971-07-08 | 1971-07-08 | Process for the manufacture of benzodiazepine derivatives |
| US18750071A | 1971-10-07 | 1971-10-07 | |
| US18750071 | 1971-10-07 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FI57258B FI57258B (fi) | 1980-03-31 |
| FI57258C true FI57258C (fi) | 1980-07-10 |
Family
ID=26261215
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI1932/72A FI57258C (fi) | 1971-07-08 | 1972-07-07 | Foerfarande foer framstaellning av 1,3-dihydro-5-pyridyl-2h-1,4-bensodiazepin-derivat |
Country Status (17)
| Country | Link |
|---|---|
| JP (1) | JPS5331878B1 (da) |
| AR (1) | AR192656A1 (da) |
| AT (1) | AT327198B (da) |
| AU (1) | AU458347B2 (da) |
| BE (1) | BE785963A (da) |
| CH (1) | CH569007A5 (da) |
| DK (1) | DK147482C (da) |
| ES (1) | ES404626A1 (da) |
| FI (1) | FI57258C (da) |
| FR (1) | FR2144830A1 (da) |
| HU (1) | HU166414B (da) |
| IE (1) | IE36734B1 (da) |
| IL (1) | IL39844A (da) |
| NL (1) | NL164282C (da) |
| NO (1) | NO132320C (da) |
| SE (2) | SE416807B (da) |
| YU (1) | YU177072A (da) |
-
0
- BE BE785963D patent/BE785963A/xx not_active IP Right Cessation
-
1972
- 1972-06-09 CH CH859572A patent/CH569007A5/xx not_active IP Right Cessation
- 1972-07-03 IE IE926/72A patent/IE36734B1/xx unknown
- 1972-07-06 IL IL39844A patent/IL39844A/xx unknown
- 1972-07-06 YU YU01770/72A patent/YU177072A/xx unknown
- 1972-07-06 FR FR7224437A patent/FR2144830A1/fr active Granted
- 1972-07-07 ES ES404626A patent/ES404626A1/es not_active Expired
- 1972-07-07 SE SE7209050A patent/SE416807B/xx unknown
- 1972-07-07 AT AT584472A patent/AT327198B/de not_active IP Right Cessation
- 1972-07-07 AR AR242957A patent/AR192656A1/es active
- 1972-07-07 JP JP6811472A patent/JPS5331878B1/ja active Pending
- 1972-07-07 NO NO2454/72A patent/NO132320C/no unknown
- 1972-07-07 HU HUHO1496A patent/HU166414B/hu unknown
- 1972-07-07 AU AU44361/72A patent/AU458347B2/en not_active Expired
- 1972-07-07 DK DK341372A patent/DK147482C/da active
- 1972-07-07 SE SE7209051A patent/SE416651B/xx unknown
- 1972-07-07 NL NL7209490.A patent/NL164282C/xx not_active IP Right Cessation
- 1972-07-07 FI FI1932/72A patent/FI57258C/fi active
Also Published As
| Publication number | Publication date |
|---|---|
| AU4436172A (en) | 1974-01-10 |
| ATA584472A (de) | 1975-04-15 |
| DK147482B (da) | 1984-08-27 |
| NL164282C (nl) | 1980-12-15 |
| DE2233483B2 (de) | 1977-03-24 |
| NO132320B (da) | 1975-07-14 |
| YU177072A (en) | 1982-02-25 |
| HU166414B (da) | 1975-03-28 |
| IL39844A0 (en) | 1972-09-28 |
| DK147482C (da) | 1985-03-25 |
| IE36734L (en) | 1973-01-08 |
| FR2144830B1 (da) | 1975-11-28 |
| AR192656A1 (es) | 1973-02-28 |
| NL7209490A (da) | 1973-01-10 |
| BE785963A (fr) | 1973-01-08 |
| NL164282B (nl) | 1980-07-15 |
| IE36734B1 (en) | 1977-02-16 |
| DE2233483A1 (de) | 1973-01-25 |
| NO132320C (da) | 1975-10-22 |
| FI57258B (fi) | 1980-03-31 |
| ES404626A1 (es) | 1975-11-16 |
| FR2144830A1 (en) | 1973-02-16 |
| AT327198B (de) | 1976-01-26 |
| SE416807B (sv) | 1981-02-09 |
| SE416651B (sv) | 1981-01-26 |
| IL39844A (en) | 1976-07-30 |
| AU458347B2 (en) | 1975-02-27 |
| JPS5331878B1 (da) | 1978-09-05 |
| CH569007A5 (da) | 1975-11-14 |
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