DD220310A5 - Verfahren zur herstellung von triazol (2,3-c)(1,3) benzodiazepinen) - Google Patents

Verfahren zur herstellung von triazol (2,3-c)(1,3) benzodiazepinen) Download PDF

Info

Publication number: DD220310A5
Authority: DD; German Democratic Republic
Prior art keywords: hydrogen; lower alkyl; methyl; formula; low
Prior art date: 1983-06-06

Application number

DD84263805A

Other languages

German (de)

English (en)

Inventor

Isidoros Vlattas

Original Assignee

Ciba Geigy Ag

Priority date (The priority date 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 date listed.)

1983-06-06

Filing date

1984-06-05

Publication date

1985-03-27

1984-06-05 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1985-03-27 Publication of DD220310A5 publication Critical patent/DD220310A5/de

Links

FMMHUIFSJWVNAE-UHFFFAOYSA-N 1h-1,3-benzodiazepine Chemical compound N1C=NC=CC2=CC=CC=C12 FMMHUIFSJWVNAE-UHFFFAOYSA-N 0.000 title description 5
238000004519 manufacturing process Methods 0.000 title description 2
QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 110
-1 AMINO Chemical class 0.000 claims abstract description 78
125000000217 alkyl group Chemical group 0.000 claims abstract description 72
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 61
239000001257 hydrogen Substances 0.000 claims abstract description 61
150000003839 salts Chemical class 0.000 claims abstract description 45
238000000034 method Methods 0.000 claims abstract description 33
125000003545 alkoxy group Chemical group 0.000 claims abstract description 24
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 22
229910052736 halogen Inorganic materials 0.000 claims abstract description 20
150000002367 halogens Chemical class 0.000 claims abstract description 20
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 19
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 18
125000004423 acyloxy group Chemical group 0.000 claims abstract description 9
125000003342 alkenyl group Chemical group 0.000 claims abstract description 6
125000000304 alkynyl group Chemical group 0.000 claims abstract description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 4
125000004104 aryloxy group Chemical group 0.000 claims abstract description 3
125000001589 carboacyl group Chemical group 0.000 claims abstract 3
239000000203 mixture Substances 0.000 claims description 48
150000002431 hydrogen Chemical class 0.000 claims description 37
125000004414 alkyl thio group Chemical group 0.000 claims description 19
229940049706 benzodiazepine Drugs 0.000 claims description 19
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
238000002360 preparation method Methods 0.000 claims description 18
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 18
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 16
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 15
150000001204 N-oxides Chemical class 0.000 claims description 13
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 12
125000002252 acyl group Chemical group 0.000 claims description 11
230000008569 process Effects 0.000 claims description 11
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 10
239000005977 Ethylene Substances 0.000 claims description 10
229910052783 alkali metal Inorganic materials 0.000 claims description 9
150000001340 alkali metals Chemical class 0.000 claims description 9
125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
150000003852 triazoles Chemical class 0.000 claims description 7
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 5
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 5
125000001309 chloro group Chemical group Cl* 0.000 claims description 5
229910052757 nitrogen Inorganic materials 0.000 claims description 5
125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 3
125000002947 alkylene group Chemical group 0.000 claims description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 2
QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims description 2
GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 2
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
125000003282 alkyl amino group Chemical group 0.000 claims description 2
125000005153 alkyl sulfamoyl group Chemical group 0.000 claims description 2
125000001153 fluoro group Chemical group F* 0.000 claims description 2
DDCYYCUMAFYDDU-UHFFFAOYSA-N methyl thiohypochlorite Chemical compound CSCl DDCYYCUMAFYDDU-UHFFFAOYSA-N 0.000 claims description 2
230000003287 optical effect Effects 0.000 claims description 2
229910052760 oxygen Inorganic materials 0.000 claims description 2
239000001301 oxygen Substances 0.000 claims description 2
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 2
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 2
229910052717 sulfur Inorganic materials 0.000 claims description 2
125000004434 sulfur atom Chemical group 0.000 claims description 2
GCKMFJBGXUYNAG-HLXURNFRSA-N Methyltestosterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@](C)(O)[C@@]1(C)CC2 GCKMFJBGXUYNAG-HLXURNFRSA-N 0.000 claims 1
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract description 5
230000003266 anti-allergic effect Effects 0.000 abstract description 4
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230000001225 therapeutic effect Effects 0.000 abstract description 2
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WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical class F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 abstract 2
KKFDJZZADQONDE-UHFFFAOYSA-N (hydridonitrato)hydroxidocarbon(.) Chemical class O[C]=N KKFDJZZADQONDE-UHFFFAOYSA-N 0.000 abstract 1
GQPLMRYTRLFLPF-UHFFFAOYSA-N nitrous oxide Inorganic materials [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 72
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239000000243 solution Substances 0.000 description 35
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 33
239000007858 starting material Substances 0.000 description 29
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 26
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
239000002253 acid Substances 0.000 description 23
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
238000002844 melting Methods 0.000 description 21
230000008018 melting Effects 0.000 description 21
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 description 13
229910052943 magnesium sulfate Inorganic materials 0.000 description 13
235000019341 magnesium sulphate Nutrition 0.000 description 13
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
239000000284 extract Substances 0.000 description 12
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 description 11
239000002585 base Substances 0.000 description 11
150000007513 acids Chemical class 0.000 description 10
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 10
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
239000000725 suspension Substances 0.000 description 10
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 10
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 9
239000000460 chlorine Substances 0.000 description 9
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 8
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238000006243 chemical reaction Methods 0.000 description 8
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 7
241001465754 Metazoa Species 0.000 description 7
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 7
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
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VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
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239000004480 active ingredient Substances 0.000 description 6
230000001387 anti-histamine Effects 0.000 description 6
239000003610 charcoal Substances 0.000 description 6
239000000706 filtrate Substances 0.000 description 6
239000000543 intermediate Substances 0.000 description 6
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 6
238000010992 reflux Methods 0.000 description 6
239000011734 sodium Substances 0.000 description 6
239000002904 solvent Substances 0.000 description 6
238000003756 stirring Methods 0.000 description 6
PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 5
XDSFEVFCNJALNV-BTJKTKAUSA-N 1h-1,2-benzodiazepine;(z)-but-2-enedioic acid Chemical compound OC(=O)\C=C/C(O)=O.N1N=CC=CC2=CC=CC=C12 XDSFEVFCNJALNV-BTJKTKAUSA-N 0.000 description 5
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 5
229920002472 Starch Polymers 0.000 description 5
125000005907 alkyl ester group Chemical group 0.000 description 5
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HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 5
229910000027 potassium carbonate Inorganic materials 0.000 description 5
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239000003054 catalyst Substances 0.000 description 4
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229940093915 gynecological organic acid Drugs 0.000 description 4
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YSWJVSQCDZOIJL-UHFFFAOYSA-N 3-[(2-isothiocyanatophenyl)methyl]-5-methyl-1h-1,2,4-triazole Chemical compound N1C(C)=NC(CC=2C(=CC=CC=2)N=C=S)=N1 YSWJVSQCDZOIJL-UHFFFAOYSA-N 0.000 description 3
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
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ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 3
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CELPHAGZKFMOMR-UHFFFAOYSA-N azanium;dichloromethane;methanol;hydroxide Chemical compound [NH4+].[OH-].OC.ClCCl CELPHAGZKFMOMR-UHFFFAOYSA-N 0.000 description 2
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PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
150000004967 organic peroxy acids Chemical class 0.000 description 1
230000003204 osmotic effect Effects 0.000 description 1
150000002924 oxiranes Chemical group 0.000 description 1
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000006072 paste Substances 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
XCRBXWCUXJNEFX-UHFFFAOYSA-N peroxybenzoic acid Chemical class OOC(=O)C1=CC=CC=C1 XCRBXWCUXJNEFX-UHFFFAOYSA-N 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
229960005323 phenoxyethanol Drugs 0.000 description 1
AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 1
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 1
OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical class OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
229910003446 platinum oxide Inorganic materials 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
229910000105 potassium hydride Inorganic materials 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002243 precursor Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
239000008213 purified water Substances 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
230000009467 reduction Effects 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
230000004044 response Effects 0.000 description 1
238000007142 ring opening reaction Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
210000003625 skull Anatomy 0.000 description 1
235000010413 sodium alginate Nutrition 0.000 description 1
239000000661 sodium alginate Substances 0.000 description 1
229940005550 sodium alginate Drugs 0.000 description 1
239000012419 sodium bis(2-methoxyethoxy)aluminum hydride Substances 0.000 description 1
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
235000002639 sodium chloride Nutrition 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
235000010356 sorbitol Nutrition 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
229960004793 sucrose Drugs 0.000 description 1
125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
150000003458 sulfonic acid derivatives Chemical class 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
125000001425 triazolyl group Chemical group 0.000 description 1
238000005303 weighing Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D249/12—Oxygen or sulfur atoms
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Public Health (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Pulmonology (AREA)
Immunology (AREA)
Psychiatry (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Plural Heterocyclic Compounds (AREA)
Steroid Compounds (AREA)

DD84263805A 1983-06-06 1984-06-05 Verfahren zur herstellung von triazol (2,3-c)(1,3) benzodiazepinen) DD220310A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US50132883A	1983-06-06	1983-06-06

Publications (1)

Publication Number	Publication Date
DD220310A5 true DD220310A5 (de)	1985-03-27

Family

ID=23993078

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD84263805A DD220310A5 (de)	1983-06-06	1984-06-05	Verfahren zur herstellung von triazol (2,3-c)(1,3) benzodiazepinen)

Country Status (17)

Country	Link
EP (1)	EP0129509B1 (fr)
JP (1)	JPS606689A (fr)
AT (1)	ATE45740T1 (fr)
AU (1)	AU574075B2 (fr)
CA (1)	CA1215044A (fr)
DD (1)	DD220310A5 (fr)
DE (1)	DE3479499D1 (fr)
DK (1)	DK276484A (fr)
ES (1)	ES533135A0 (fr)
FI (1)	FI78098C (fr)
GR (1)	GR82058B (fr)
HU (1)	HU190930B (fr)
IL (1)	IL72015A (fr)
NO (1)	NO162070C (fr)
NZ (1)	NZ208373A (fr)
PT (1)	PT78687A (fr)
ZA (1)	ZA844186B (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IL84093A (en) *	1986-10-09	1992-09-06	Ciba Geigy Ag	Aralkyl-4h-1,2,4-triazole derivatives,their preparation and pharmaceutical compositions containing them
DE19824673A1 (de) *	1998-05-26	1999-12-02	Schering Ag	Neue 2,3-Benzodiazepinderivate, deren Herstellung und Verwendung als Arzneimittel

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3539573A (en) *	1967-03-22	1970-11-10	Jean Schmutz	11-basic substituted dibenzodiazepines and dibenzothiazepines
US4076823A (en) *	1977-08-18	1978-02-28	E. R. Squibb & Sons, Inc.	Triazolo-2,4-benzodiazepines
US4192803A (en) *	1978-09-15	1980-03-11	American Cyanamid Company	5H-Pyrrolo[2,1-c][1,4]benzodiazepine derivatives
FI824170A7 (fi) *	1981-12-07	1983-06-08	Ciba Geigy Ag	Imidatsobensodiatsepiinit, menetelmä niiden valmistamiseksi, näitä yhdisteitä sisältävät farmaseuttiset valvalmisteet ja niiden terapeuttinen käyttö.

1984
- 1984-05-29 AT AT84810264T patent/ATE45740T1/de not_active IP Right Cessation
- 1984-05-29 EP EP84810264A patent/EP0129509B1/fr not_active Expired
- 1984-05-29 DE DE8484810264T patent/DE3479499D1/de not_active Expired
- 1984-06-04 IL IL72015A patent/IL72015A/xx unknown
- 1984-06-04 GR GR74912A patent/GR82058B/el unknown
- 1984-06-04 CA CA000455776A patent/CA1215044A/fr not_active Expired
- 1984-06-04 FI FI842228A patent/FI78098C/fi not_active IP Right Cessation
- 1984-06-04 DK DK276484A patent/DK276484A/da not_active Application Discontinuation
- 1984-06-04 PT PT78687A patent/PT78687A/pt not_active IP Right Cessation
- 1984-06-05 NZ NZ208373A patent/NZ208373A/en unknown
- 1984-06-05 ES ES533135A patent/ES533135A0/es active Granted
- 1984-06-05 DD DD84263805A patent/DD220310A5/de not_active IP Right Cessation
- 1984-06-05 HU HU842181A patent/HU190930B/hu unknown
- 1984-06-05 ZA ZA844186A patent/ZA844186B/xx unknown
- 1984-06-05 NO NO842254A patent/NO162070C/no unknown
- 1984-06-05 AU AU29106/84A patent/AU574075B2/en not_active Ceased
- 1984-06-06 JP JP59114697A patent/JPS606689A/ja active Granted

Also Published As

Publication number	Publication date
ES8506713A1 (es)	1985-08-01
NO162070B (no)	1989-07-24
PT78687A (en)	1984-07-01
GR82058B (fr)	1984-12-13
EP0129509B1 (fr)	1989-08-23
AU2910684A (en)	1984-12-13
EP0129509A3 (en)	1985-09-11
HU190930B (en)	1986-12-28
ZA844186B (en)	1985-02-27
IL72015A0 (en)	1984-10-31
JPH0354669B2 (fr)	1991-08-20
EP0129509A2 (fr)	1984-12-27
ATE45740T1 (de)	1989-09-15
CA1215044A (fr)	1986-12-09
FI842228A0 (fi)	1984-06-04
NZ208373A (en)	1987-02-20
IL72015A (en)	1987-12-31
JPS606689A (ja)	1985-01-14
ES533135A0 (es)	1985-08-01
FI78098B (fi)	1989-02-28
HUT34488A (en)	1985-03-28
DK276484D0 (da)	1984-06-04
NO162070C (no)	1989-11-01
DE3479499D1 (en)	1989-09-28
FI842228A7 (fi)	1984-12-07
NO842254L (no)	1984-12-07
DK276484A (da)	1984-12-07
AU574075B2 (en)	1988-06-30
FI78098C (fi)	1989-06-12

Legal Events

Date	Code	Title	Description
1995-06-08	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
DE3502508C2 (fr)	1990-05-03
DE69407176T2 (de)	1998-07-02	Antipsychotische benzimidazolderivate
DE2940483C2 (fr)	1989-06-22
DE3788385T2 (de)	1994-05-11	Pyrimidin-Derivate.
CH649539A5 (de)	1985-05-31	Antidepressiv wirksame piperazinylalkyl-1,2,4-triazol-3-one.
DE3423898A1 (de)	1985-01-03	Piperazinyl-alkyl-1,2,4-triazol-3-on-derivate, verfahren zu deren herstellung und diese verbindungen enthaltende pharmazeutische mittel
DE1795062A1 (de)	1972-03-30	1H-Imidazo[4,5-b]pyrazin-2-one und Verfahren zu ihrer Herstellung
DE2302717A1 (de)	1973-07-26	Heterocyclische verbindungen
DD213920A5 (de)	1984-09-26	Verfahren zur herstellung von dihydropyridinen
DE2628189A1 (de)	1977-01-20	3-phenylindoline, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
EP1176144B1 (fr)	2003-07-09	Dérivés de N-triazolylméthyl-piperazine, en tant qu' antagonistes récepteurs de la neuroquinine
CH656127A5 (de)	1986-06-13	Substituierte pyrazolochinoline, verfahren zu ihrer herstellung und pharmazeutische praeparate enthaltend diese verbindungen.
DE60111568T2 (de)	2006-05-11	Tetrahydro-(benzo- oder thieno-)azepin-pyrazin und triazinderivative als mglur 1 antagonisten
DE69310904T2 (de)	1997-08-28	Verbrückte bis-aryl-carbinol-derivate, zusammensetzungen und ihre verwendung
DE1670305C3 (de)	1982-03-25	5-Phenyl-2,4-dioxo-1,2,3,4-tetrahydro-3H-1,5-benzodiazepine und Verfahren zu ihrer Herstellung
EP0445073A1 (fr)	1991-09-04	Benzofurannes
DD282457A5 (de)	1990-09-12	Verfahren zur herstellung neuer heterocyclischer derivate
DD220310A5 (de)	1985-03-27	Verfahren zur herstellung von triazol (2,3-c)(1,3) benzodiazepinen)
EP0042354B1 (fr)	1985-12-11	Imidazobenzothiadiazépines, procédé pour leur préparation et compositions pharmaceutiques les contenant
EP0233483A2 (fr)	1987-08-26	Pyrrolo[1,2-a][4,1]benzoxazépines, procédé pour leur préparation, compositions pharmaceutiques contenant ces composés et application therapeutique
DE60002395T2 (de)	2004-04-08	Metalloproteaseinhibitoren, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Zubereitungen
DE3404193C2 (fr)	1987-06-11
DE69324794T2 (de)	1999-12-02	Phenyl imidazolinon-derivate, verfahren zu ihrer herstellung und ihre verwendung als 5-ht3-rezeptor-antagonisten
EP0081461A2 (fr)	1983-06-15	Imidazobenzodiazépines, procédé pour leur préparation, préparations pharmaceutiques contenant ces composés et leur utilisation thérapeutique
DE68903465T4 (de)	1994-02-10	Tricyclische Aromatasehemmer.