CH505138A - Procédé de préparation de benzodiazèpines - Google Patents

Procédé de préparation de benzodiazèpines

Info

Publication number: CH505138A
Authority: CH; Switzerland
Prior art keywords: lower alkyl; chloro; benzodiazepin; group; mixture
Prior art date: 1968-10-24

Application number

CH1592169A

Other languages

English (en)

French (fr)

Inventor

Tachikawa Ryuji

Takagi Hiromu

Miyadera Tetsuo

Kamioka Toshiharu

Fukunaga Mitsunobu

Kawano Yoichi

Original Assignee

Sankyo Co

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.)

1968-10-24

Filing date

1969-10-24

Publication date

1971-03-31

1969-10-24 Application filed by Sankyo Co filed Critical Sankyo Co

1971-03-31 Publication of CH505138A publication Critical patent/CH505138A/fr

Links

125000000217 alkyl group Chemical group 0.000 claims abstract description 37
-1 CO2-alkyl CONH2 Chemical group 0.000 claims abstract description 28
229940049706 benzodiazepine Drugs 0.000 claims abstract description 17
125000002252 acyl group Chemical group 0.000 claims abstract description 6
125000003118 aryl group Chemical group 0.000 claims abstract description 6
125000003545 alkoxy group Chemical group 0.000 claims abstract description 5
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 3
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 27
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 27
239000002904 solvent Substances 0.000 claims description 21
238000010992 reflux Methods 0.000 claims description 20
SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 claims description 12
238000000034 method Methods 0.000 claims description 9
239000012965 benzophenone Substances 0.000 claims description 7
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 7
239000003960 organic solvent Substances 0.000 claims description 7
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
125000004442 acylamino group Chemical group 0.000 claims description 3
125000004423 acyloxy group Chemical group 0.000 claims description 3
125000005843 halogen group Chemical group 0.000 claims description 3
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 3
RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 2
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
125000004093 cyano group Chemical group *C#N 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
238000004519 manufacturing process Methods 0.000 claims 1
238000007363 ring formation reaction Methods 0.000 claims 1
125000000446 sulfanediyl group Chemical group *S* 0.000 claims 1
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract description 10
150000001557 benzodiazepines Chemical class 0.000 abstract description 5
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract description 5
125000003710 aryl alkyl group Chemical group 0.000 abstract description 3
230000001430 anti-depressive effect Effects 0.000 abstract description 2
239000000935 antidepressant agent Substances 0.000 abstract description 2
229940005513 antidepressants Drugs 0.000 abstract description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 abstract 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 abstract 1
XAKBSHICSHRJCL-UHFFFAOYSA-N [CH2]C(=O)C1=CC=CC=C1 Chemical group [CH2]C(=O)C1=CC=CC=C1 XAKBSHICSHRJCL-UHFFFAOYSA-N 0.000 abstract 1
239000003513 alkali Substances 0.000 abstract 1
239000002585 base Substances 0.000 abstract 1
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 abstract 1
230000005494 condensation Effects 0.000 abstract 1
238000009833 condensation Methods 0.000 abstract 1
150000002148 esters Chemical group 0.000 abstract 1
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 87
239000000047 product Substances 0.000 description 36
239000000203 mixture Substances 0.000 description 34
239000000155 melt Substances 0.000 description 31
239000011541 reaction mixture Substances 0.000 description 23
238000006243 chemical reaction Methods 0.000 description 22
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 17
238000000354 decomposition reaction Methods 0.000 description 13
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 12
238000004821 distillation Methods 0.000 description 12
NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 11
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 10
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
229910000027 potassium carbonate Inorganic materials 0.000 description 8
239000013078 crystal Substances 0.000 description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
239000013067 intermediate product Substances 0.000 description 6
229910000029 sodium carbonate Inorganic materials 0.000 description 6
RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 5
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
239000002253 acid Substances 0.000 description 4
239000007795 chemical reaction product Substances 0.000 description 4
238000002360 preparation method Methods 0.000 description 4
239000000741 silica gel Substances 0.000 description 4
229910002027 silica gel Inorganic materials 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
PKSVTEMCGNQIMD-UHFFFAOYSA-N (2-aminophenyl)-(2-chlorophenyl)methanone Chemical compound NC1=CC=CC=C1C(=O)C1=CC=CC=C1Cl PKSVTEMCGNQIMD-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
125000003277 amino group Chemical group 0.000 description 3
230000000694 effects Effects 0.000 description 3
230000035484 reaction time Effects 0.000 description 3
PEGJZBBHDJDXEP-UHFFFAOYSA-N 1-(2-amino-3-benzoyl-5-chlorophenyl)-2-bromoethanone Chemical compound ClC=1C=C(C(=C(C(=O)C2=CC=CC=C2)C1)N)C(CBr)=O PEGJZBBHDJDXEP-UHFFFAOYSA-N 0.000 description 2
125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
239000007810 chemical reaction solvent Substances 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
125000001841 imino group Chemical group [H]N=* 0.000 description 2
238000002955 isolation Methods 0.000 description 2
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 2
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
239000002516 radical scavenger Substances 0.000 description 2
239000001632 sodium acetate Substances 0.000 description 2
235000017281 sodium acetate Nutrition 0.000 description 2
239000007858 starting material Substances 0.000 description 2
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 2
125000004149 thio group Chemical group *S* 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
230000002936 tranquilizing effect Effects 0.000 description 2
NRAJMXHXQHCBHO-UHFFFAOYSA-N (2-aminophenyl)-(2-fluorophenyl)methanone Chemical compound NC1=CC=CC=C1C(=O)C1=CC=CC=C1F NRAJMXHXQHCBHO-UHFFFAOYSA-N 0.000 description 1
CKCNELPOXRQRDT-UHFFFAOYSA-N (2-aminophenyl)-(4-nitrophenyl)methanone Chemical compound NC1=CC=CC=C1C(=O)C1=CC=C([N+]([O-])=O)C=C1 CKCNELPOXRQRDT-UHFFFAOYSA-N 0.000 description 1
MAOBFOXLCJIFLV-UHFFFAOYSA-N (2-aminophenyl)-phenylmethanone Chemical compound NC1=CC=CC=C1C(=O)C1=CC=CC=C1 MAOBFOXLCJIFLV-UHFFFAOYSA-N 0.000 description 1
ROXAFEIDZVHGFX-UHFFFAOYSA-N 1,3,4,5-tetrahydro-1,4-benzodiazepin-2-one Chemical compound N1C(=O)CNCC2=CC=CC=C21 ROXAFEIDZVHGFX-UHFFFAOYSA-N 0.000 description 1
USXTZTSZNRIVAG-UHFFFAOYSA-N 1-[2-amino-5-chloro-3-(2-chlorobenzoyl)phenyl]-2-bromoethanone Chemical compound ClC=1C=C(C(=C(C(=O)C2=C(C=CC=C2)Cl)C=1)N)C(CBr)=O USXTZTSZNRIVAG-UHFFFAOYSA-N 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
125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 1
CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
CDHRYNHYMHKSSY-UHFFFAOYSA-N ClC=1C=CC(=C(C(=O)C2=C(C=CC=C2)NC(=O)C)C1)Br Chemical compound ClC=1C=CC(=C(C(=O)C2=C(C=CC=C2)NC(=O)C)C1)Br CDHRYNHYMHKSSY-UHFFFAOYSA-N 0.000 description 1
FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
AGKPGIOZNCJFTQ-UHFFFAOYSA-N [2-(methylamino)phenyl]-phenylmethanone Chemical compound CNC1=CC=CC=C1C(=O)C1=CC=CC=C1 AGKPGIOZNCJFTQ-UHFFFAOYSA-N 0.000 description 1
238000013019 agitation Methods 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
150000001412 amines Chemical class 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
238000009835 boiling Methods 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
125000004744 butyloxycarbonyl group Chemical group 0.000 description 1
125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
210000003169 central nervous system Anatomy 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
125000006125 ethylsulfonyl group Chemical group 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
238000001640 fractional crystallisation Methods 0.000 description 1
150000002466 imines Chemical class 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
231100000053 low toxicity Toxicity 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
125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 description 1
MRXZRJQRQWTKIX-UHFFFAOYSA-N n-(2-benzoylphenyl)acetamide Chemical compound CC(=O)NC1=CC=CC=C1C(=O)C1=CC=CC=C1 MRXZRJQRQWTKIX-UHFFFAOYSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001038 naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
125000005425 toluyl group Chemical group 0.000 description 1
239000003204 tranquilizing agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D203/00—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom
- C07D203/04—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D203/06—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D203/08—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no 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 the ring nitrogen atom
- 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)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

CH1592169A 1968-10-24 1969-10-24 Procédé de préparation de benzodiazèpines CH505138A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP43077505A JPS4834757B1 (de)	1968-10-24	1968-10-24

Publications (1)

Publication Number	Publication Date
CH505138A true CH505138A (fr)	1971-03-31

Family

ID=13635807

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1592169A CH505138A (fr)	1968-10-24	1969-10-24	Procédé de préparation de benzodiazèpines

Country Status (7)

Country	Link
JP (1)	JPS4834757B1 (de)
BR (1)	BR6913582D0 (de)
CH (1)	CH505138A (de)
CS (1)	CS172316B2 (de)
IN (1)	IN123679B (de)
NL (1)	NL6915995A (de)
SE (1)	SE350505B (de)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2119072A1 (de) *	1970-12-23	1972-08-04	Hoffmann La Roche

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS51146068U (de) *	1975-05-17	1976-11-24

1968
- 1968-10-24 JP JP43077505A patent/JPS4834757B1/ja active Pending
1969
- 1969-10-23 NL NL6915995A patent/NL6915995A/xx unknown
- 1969-10-23 BR BR21358269A patent/BR6913582D0/pt unknown
- 1969-10-23 IN IN123679A patent/IN123679B/en unknown
- 1969-10-24 CH CH1592169A patent/CH505138A/fr not_active IP Right Cessation
- 1969-10-24 CS CS706269A patent/CS172316B2/cs unknown
- 1969-10-24 SE SE1461669A patent/SE350505B/xx unknown

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2119072A1 (de) *	1970-12-23	1972-08-04	Hoffmann La Roche

Also Published As

Publication number	Publication date
IN123679B (de)	1975-09-06
JPS4834757B1 (de)	1973-10-23
CS172316B2 (de)	1976-12-29
NL6915995A (de)	1970-04-28
BR6913582D0 (pt)	1973-02-15
SE350505B (de)	1972-10-30

Legal Events

Date	Code	Title	Description
1978-05-31	PL	Patent ceased

Publication	Publication Date	Title
EP0097071B1 (de)	1985-08-28	Benzhydrylsulfinylacetamid-Derivate und deren Verwendung in der Therapeutik
EP0340064B1 (de)	1993-03-17	Benzodiazepine, Verfahren und Zwischenprodukte zu ihrer Herstellung und ihre therapeutische Verwendung
EP0003383B1 (de)	1983-02-09	4-Amino-3-Sulfonamido Pyridinderivate
EP0373998B1 (de)	1993-08-11	Propenonoximether, Verfahren zu dessen Herstellung sowie diese enthaltende Arzneinmittel
EP0117794A1 (de)	1984-09-05	2-Amino-5-phenyl-1,3-benzodiazepine, Verfahren zu ihrer Herstellung und sie enthaltende Arzneimittel
FR2591596A1 (fr)	1987-06-19	Nouvelles 4h-triazolo(4,3-a)(1,4)benzodiazepines, leur procede de preparation, leur application comme medicaments et les compositions les renfermant
EP0343050B1 (de)	1992-12-02	6-Phenyl-3-piperazinylalkyl-1H,3H-pyrimidindion-2,4-Derivate, deren Herstellung und Verwendung als Heilmittel
FR2639044A1 (fr)	1990-05-18	Derives de la butynylamine
FR2618150A1 (fr)	1989-01-20	Benzazepines 3-substituees a action therapeutique
EP0495709A1 (de)	1992-07-22	Aryltriazinverbindungen, Verfahren zu ihrer Herstellung und pharmazeutische Zusammensetzungen die sie enthalten
CH505138A (fr)	1971-03-31	Procédé de préparation de benzodiazèpines
CH616647A5 (de)	1980-04-15
EP0002978A2 (de)	1979-07-11	Thiazolidindion-2,4 Derivate, deren Herstellung und Verwendung als Arzneimittel
EP0998470B1 (de)	2003-05-07	Verfahren zur herstellung von alkoxyfuranon-amin-derivaten, durch dieses verfahren erhaltene verbindungen und verwendung dieser verbindungen
EP0045251B1 (de)	1983-11-30	Thiazolo(3,2-a)pyrimidinderivate, ihre Herstellung und Arzneimittel, die diese Derivate enthalten
FR2566774A1 (fr)	1986-01-03	Derives de 5h-2,3-benzodiazepine, leur procede de preparation et compositions pharmaceutiques les contenant
CA1115294A (fr)	1981-12-29	Procede de preparation de nouveaux derives de la 5h-benzocyclohepten-7-amine et leurs sels
EP0067094B1 (de)	1985-10-02	Heterocyclische Derivate von Amidoxinen, ihre Herstellung und therapeutische Verwendung
CH620912A5 (de)	1980-12-31
EP0035619B1 (de)	1984-07-25	3-Amino-(1H,3H)-2,4-chinazolindionderivate
EP0395527B1 (de)	1994-09-14	Imidazobenzodiazepine und ihre Salze, Verfahren zur Herstellung, Verwendung als Arzneimittel und diese Substanzen enthaltende Zusammensetzungen
EP0043811B1 (de)	1985-03-20	Indolonaphthyridine und ihre Verwendung als Arzneimittel
EP0955310B1 (de)	2004-10-13	Neue (3,4,7,8,9,10) hexahydro-6, 10-dioxo-6H-pyridazino /1, 2-a/ /1, 2/ Diazepin-1-Carbonsäure-Derivate, Verfahren zu deren Herstellung und deren Verwendung zur Herstellung pharmazeutischer Wirkstoffe
EP0017523B1 (de)	1982-09-01	Derivate des Dithiepinno (1,4)(2,3-c) pyrrols, ihre Herstellung und sie enthaltende Medikamente
FR2672888A1 (fr)	1992-08-21	Nouvelles urees et thiourees, leur preparation et leur application en therapeutique.

CH505138A - Procédé de préparation de benzodiazèpines - Google Patents

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