NO124035B - - Google Patents

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Info

Publication number: NO124035B
Authority: NO; Norway
Prior art keywords: parts; derivatives; acid; volume; solvent
Prior art date: 1968-09-03

Application number

NO3505/69A

Other languages

English (en)

Norwegian (no)

Inventor

K Meguro

H Tawada

Y Kuwada

T Maduda

Original Assignee

Takeda Chemical Industries Ltd

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.)

1968-09-03

Filing date

1969-09-02

Publication date

1972-02-21

1969-09-02 Application filed by Takeda Chemical Industries Ltd filed Critical Takeda Chemical Industries Ltd

1972-02-21 Publication of NO124035B publication Critical patent/NO124035B/no

Links

125000000217 alkyl group Chemical group 0.000 claims description 10
238000000034 method Methods 0.000 claims description 8
ZIZZRIVYGYSIKB-UHFFFAOYSA-N 2-hydroxy-1,2-benzodiazepine Chemical class ON1C=CC=C2C=CC=CC2=N1 ZIZZRIVYGYSIKB-UHFFFAOYSA-N 0.000 claims description 5
230000007062 hydrolysis Effects 0.000 claims description 5
238000006460 hydrolysis reaction Methods 0.000 claims description 5
125000003545 alkoxy group Chemical group 0.000 claims description 3
229940053197 benzodiazepine derivative antiepileptics Drugs 0.000 claims description 3
229910052736 halogen Inorganic materials 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
238000007363 ring formation reaction Methods 0.000 claims description 3
125000001424 substituent group Chemical group 0.000 claims description 3
150000002367 halogens Chemical class 0.000 claims description 2
238000002360 preparation method Methods 0.000 claims description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
125000003310 benzodiazepinyl group Chemical class N1N=C(C=CC2=C1C=CC=C2)* 0.000 claims 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 19
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
239000000203 mixture Substances 0.000 description 13
239000002904 solvent Substances 0.000 description 13
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
239000013078 crystal Substances 0.000 description 11
238000002844 melting Methods 0.000 description 10
230000008018 melting Effects 0.000 description 10
-1 propy-T Chemical group 0.000 description 9
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
229960000583 acetic acid Drugs 0.000 description 8
239000002253 acid Substances 0.000 description 7
230000003647 oxidation Effects 0.000 description 6
238000007254 oxidation reaction Methods 0.000 description 6
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
229940117975 chromium trioxide Drugs 0.000 description 5
WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 5
GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 description 5
239000012362 glacial acetic acid Substances 0.000 description 5
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
229910000041 hydrogen chloride Inorganic materials 0.000 description 5
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
150000001875 compounds Chemical class 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
150000003839 salts Chemical class 0.000 description 4
229910052938 sodium sulfate Inorganic materials 0.000 description 4
235000011152 sodium sulphate Nutrition 0.000 description 4
HJKLEAOXCZIMPI-UHFFFAOYSA-N 2,2-diethoxyethanamine Chemical compound CCOC(CN)OCC HJKLEAOXCZIMPI-UHFFFAOYSA-N 0.000 description 3
YZPNFYQRPJKWFJ-UHFFFAOYSA-N 2-methyl-1h-imidazol-1-ium;chloride Chemical compound Cl.CC1=NC=CN1 YZPNFYQRPJKWFJ-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
239000007858 starting material Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-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
239000003125 aqueous solvent Substances 0.000 description 2
150000001557 benzodiazepines Chemical class 0.000 description 2
238000001816 cooling Methods 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
238000000921 elemental analysis Methods 0.000 description 2
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 2
125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
229910052740 iodine Inorganic materials 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
KJONHKAYOJNZEC-UHFFFAOYSA-N nitrazepam Chemical compound C12=CC([N+](=O)[O-])=CC=C2NC(=O)CN=C1C1=CC=CC=C1 KJONHKAYOJNZEC-UHFFFAOYSA-N 0.000 description 2
239000007800 oxidant agent Substances 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
239000000932 sedative agent Substances 0.000 description 2
GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 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 compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
DHMQDGOQFOQNFH-UHFFFAOYSA-M Aminoacetate Chemical compound NCC([O-])=O DHMQDGOQFOQNFH-UHFFFAOYSA-M 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
PBLGCNDYMWLITF-UHFFFAOYSA-N Cl.ClC=1C=CC2=C(C(=NCC(N2)O)C2=CC=CC=C2)C1 Chemical compound Cl.ClC=1C=CC2=C(C(=NCC(N2)O)C2=CC=CC=C2)C1 PBLGCNDYMWLITF-UHFFFAOYSA-N 0.000 description 1
SLEWWMBBCZFJDF-UHFFFAOYSA-N Cl.ClC=1C=CC2=C(C(=NCC(N2C)O)C2=CC=CC=C2)C1 Chemical compound Cl.ClC=1C=CC2=C(C(=NCC(N2C)O)C2=CC=CC=C2)C1 SLEWWMBBCZFJDF-UHFFFAOYSA-N 0.000 description 1
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
150000001241 acetals Chemical class 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
229940125681 anticonvulsant agent Drugs 0.000 description 1
239000001961 anticonvulsive agent Substances 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
229940092714 benzenesulfonic acid Drugs 0.000 description 1
238000009835 boiling Methods 0.000 description 1
MZJUGRUTVANEDW-UHFFFAOYSA-N bromine fluoride Chemical compound BrF MZJUGRUTVANEDW-UHFFFAOYSA-N 0.000 description 1
125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
230000001914 calming effect Effects 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
238000005859 coupling reaction Methods 0.000 description 1
AAOVKJBEBIDNHE-UHFFFAOYSA-N diazepam Chemical compound N=1CC(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 AAOVKJBEBIDNHE-UHFFFAOYSA-N 0.000 description 1
SOCTUWSJJQCPFX-UHFFFAOYSA-N dichromate(2-) Chemical class [O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O SOCTUWSJJQCPFX-UHFFFAOYSA-N 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
238000004821 distillation Methods 0.000 description 1
125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
229940093915 gynecological organic acid Drugs 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
125000002768 hydroxyalkyl group Chemical group 0.000 description 1
229940102223 injectable solution Drugs 0.000 description 1
239000011630 iodine Substances 0.000 description 1
238000002955 isolation Methods 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
229940035363 muscle relaxants Drugs 0.000 description 1
239000003158 myorelaxant agent Substances 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
125000004043 oxo group Chemical group O=* 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
229920000137 polyphosphoric acid Polymers 0.000 description 1
239000000843 powder Substances 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
238000001953 recrystallisation Methods 0.000 description 1
230000002040 relaxant effect Effects 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
150000003333 secondary alcohols Chemical class 0.000 description 1
229940125723 sedative agent Drugs 0.000 description 1
230000001624 sedative effect Effects 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
- C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
- C07D243/10—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D243/14—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines
- C07D243/16—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals
- C07D243/18—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals substituted in position 2 by nitrogen, oxygen or sulfur atoms
- C07D243/24—Oxygen atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
- B—PERFORMING OPERATIONS; TRANSPORTING
- B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05C—APPARATUS FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05C11/00—Component parts, details or accessories not specifically provided for in groups B05C1/00 - B05C9/00
- B05C11/11—Vats or other containers for liquids or other fluent materials
- B—PERFORMING OPERATIONS; TRANSPORTING
- B26—HAND CUTTING TOOLS; CUTTING; SEVERING
- B26D—CUTTING; DETAILS COMMON TO MACHINES FOR PERFORATING, PUNCHING, CUTTING-OUT, STAMPING-OUT OR SEVERING
- B26D3/00—Cutting work characterised by the nature of the cut made; Apparatus therefor
- B26D3/18—Cutting work characterised by the nature of the cut made; Apparatus therefor to obtain cubes or the like
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
- C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
- C07D243/10—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D243/14—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines
- C07D243/16—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals
- C07D243/18—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals substituted in position 2 by nitrogen, oxygen or sulfur atoms
- C07D243/24—Oxygen atoms
- C07D243/26—Preparation from compounds already containing the benzodiazepine skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
- C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
- C07D243/10—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D243/14—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines
- C07D243/16—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals
- C07D243/18—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals substituted in position 2 by nitrogen, oxygen or sulfur atoms
- C07D243/24—Oxygen atoms
- C07D243/28—Preparation including building-up the benzodiazepine skeleton from compounds containing no hetero rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
General Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Medicinal Chemistry (AREA)
Forests & Forestry (AREA)
Epidemiology (AREA)
Animal Behavior & Ethology (AREA)
Mechanical Engineering (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

NO3505/69A 1968-09-03 1969-09-02 NO124035B (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
JP6332368		1968-09-03
JP6332468		1968-09-03

Publications (1)

Publication Number	Publication Date
NO124035B true NO124035B (de)	1972-02-21

Family

ID=26404426

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO3505/69A NO124035B (de)	1968-09-03	1969-09-02

Country Status (9)

Country	Link
US (1)	US3692772A (de)
CH (1)	CH535243A (de)
DE (2)	DE1966132B2 (de)
ES (1)	ES371134A1 (de)
FR (1)	FR2017275B1 (de)
GB (2)	GB1276169A (de)
NL (1)	NL165158C (de)
NO (1)	NO124035B (de)
SE (1)	SE349807B (de)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1484661A (en) *	1975-01-06	1977-09-01	Clin Midy	Preparatin of benzodiazepine derivatives
CN110003125A (zh) *	2019-04-24	2019-07-12	湖北美林药业有限公司	一种*、*注射液及其制备方法
CN114276375A (zh) *	2021-12-15	2022-04-05	重庆医科大学	一种1,3,2-苯并二氮杂硼烷酮及其衍生物的合成方法
CN115197261B (zh) *	2022-07-06	2024-05-03	重庆医科大学	噁二氮杂硼衍生物的合成方法

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR1411072A (fr) *	1963-07-10	1965-09-17	Hoffmann La Roche	Procédé pour la préparation de dérivés de benzodiazépine
NL6409554A (de) *	1964-08-19	1966-02-21
US3558603A (en) *	1967-12-01	1971-01-26	Sumitomo Chemical Co	Process for producing benzodiazepine derivatives

1969
- 1969-08-25 SE SE11770/69A patent/SE349807B/xx unknown
- 1969-09-01 NL NL6913339.A patent/NL165158C/xx not_active IP Right Cessation
- 1969-09-02 FR FR696929938A patent/FR2017275B1/fr not_active Expired
- 1969-09-02 ES ES371134A patent/ES371134A1/es not_active Expired
- 1969-09-02 NO NO3505/69A patent/NO124035B/no unknown
- 1969-09-02 DE DE1966132A patent/DE1966132B2/de not_active Withdrawn
- 1969-09-02 DE DE1944404A patent/DE1944404C3/de not_active Expired
- 1969-09-02 CH CH1327869A patent/CH535243A/de not_active IP Right Cessation
- 1969-09-03 GB GB34002/71A patent/GB1276169A/en not_active Expired
- 1969-09-03 GB GB43519/69A patent/GB1276168A/en not_active Expired
- 1969-09-03 US US855042A patent/US3692772A/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
GB1276168A (en)	1972-06-01
FR2017275B1 (de)	1973-06-08
DE1944404C3 (de)	1979-09-13
CH535243A (de)	1973-03-31
DE1944404A1 (de)	1970-03-12
DE1944404B2 (de)	1979-01-11
GB1276169A (en)	1972-06-01
FR2017275A1 (de)	1970-05-22
DE1966132A1 (de)	1971-08-19
DE1966132B2 (de)	1981-07-23
ES371134A1 (es)	1972-01-01
NL6913339A (de)	1970-03-05
US3692772A (en)	1972-09-19
SE349807B (de)	1972-10-09
NL165158B (nl)	1980-10-15
NL165158C (nl)	1981-03-16

Publication	Publication Date	Title
Case	1951	Substituted 1, 10-Phenanthrolines. V. Phenyl derivatives
Staskun	1964	The conversion of benzoylacetanilides into 2-and 4-hydroxyquinolines
Taylor et al.	1961	Studies in Purine Chemistry. X. Some Derivatives of 9-Aminopurines1, 2
US2808413A (en)	1957-10-01	Imidazoline derivatives of 2-aryl indolines
Ardakani et al.	1983	1 H-and 2 H-indazoles by thermal and photolytic decomposition of o-azidobenzoic acid and o-azidobenzaldehyde derivatives
NO124035B (de)	1972-02-21
US2650229A (en)	1953-08-25	Derivatives of 2:3-dihydro-4-methyltfuro(3:2-c) quinoline and preparation thereof
MEGURO et al.	1973	Heterocycles. V. Syntheses and Structures of 7-Chloro-2-hydrazino-5-phenyl-3H-1, 4-benzodiazepines and Some Isomeric 1, 4, 5-Benzotriazocines
Robins et al.	1963	Aromaticity in Heterocyclic Systems. I. The Synthesis and Structure of Certain 4, 6-Dihydroxyimidazo [4, 5-c] pyridines1
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