NO118914B - - Google Patents

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Info

Publication number: NO118914B
Authority: NO; Norway
Prior art keywords: benzodiazepine; general formula; phenyl; dihydro; acid
Prior art date: 1964-08-13

Application number

NO159320A

Other languages

English (en)

Norwegian (no)

Inventor

G Archer

L Sternbach

Original Assignee

Hoffmann La Roche

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.)

1964-08-13

Filing date

1965-08-12

Publication date

1970-03-02

1965-08-12 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

1970-03-02 Publication of NO118914B publication Critical patent/NO118914B/no

Links

WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 12
150000001875 compounds Chemical class 0.000 claims description 11
238000000034 method Methods 0.000 claims description 8
239000002253 acid Substances 0.000 claims description 6
150000003839 salts Chemical class 0.000 claims description 6
239000007795 chemical reaction product Substances 0.000 claims description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
150000001557 benzodiazepines Chemical class 0.000 claims description 4
238000006243 chemical reaction Methods 0.000 claims description 4
229910052801 chlorine Inorganic materials 0.000 claims description 4
239000000460 chlorine Substances 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
AKPLHCDWDRPJGD-UHFFFAOYSA-N nordazepam Chemical compound C12=CC(Cl)=CC=C2NC(=O)CN=C1C1=CC=CC=C1 AKPLHCDWDRPJGD-UHFFFAOYSA-N 0.000 claims description 4
239000003513 alkali Substances 0.000 claims description 3
229940053197 benzodiazepine derivative antiepileptics Drugs 0.000 claims description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
LDLCZOVUSADOIV-UHFFFAOYSA-N 2-bromoethanol Chemical compound OCCBr LDLCZOVUSADOIV-UHFFFAOYSA-N 0.000 claims description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
229910052794 bromium Inorganic materials 0.000 claims description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 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
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 1
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
239000011541 reaction mixture Substances 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
238000002844 melting Methods 0.000 description 6
230000008018 melting Effects 0.000 description 6
238000001953 recrystallisation Methods 0.000 description 6
238000003756 stirring Methods 0.000 description 6
-1 7-chloro-1,3-dihydro-1-(hydroxymethyl)-5-phenyl-2H-1,4-benzodiazepine Chemical compound 0.000 description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
125000000217 alkyl group Chemical group 0.000 description 5
239000000203 mixture Substances 0.000 description 5
239000007787 solid Substances 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
150000001555 benzenes Chemical class 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
239000012141 concentrate Substances 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
229910052736 halogen Inorganic materials 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
229910052739 hydrogen Inorganic materials 0.000 description 3
239000001257 hydrogen Substances 0.000 description 3
229910052740 iodine Inorganic materials 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 2
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
239000013078 crystal Substances 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
150000002367 halogens Chemical group 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 1
GUJAGMICFDYKNR-UHFFFAOYSA-N 1,4-benzodiazepine Chemical class N1C=CN=CC2=CC=CC=C12 GUJAGMICFDYKNR-UHFFFAOYSA-N 0.000 description 1
RQFUZUMFPRMVDX-UHFFFAOYSA-N 3-Bromo-1-propanol Chemical compound OCCCBr RQFUZUMFPRMVDX-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
GSSPERGTDABVCK-UHFFFAOYSA-N 7-chloro-1-(2-hydroxyethyl)-5-phenyl-3H-1,4-benzodiazepin-2-one Chemical compound OCCN1C2=CC=C(Cl)C=C2C(=NCC1=O)C1=CC=CC=C1 GSSPERGTDABVCK-UHFFFAOYSA-N 0.000 description 1
QADHJSLAOUPYKG-UHFFFAOYSA-N 7-chloro-1-(3-hydroxypropyl)-5-phenyl-3h-1,4-benzodiazepin-2-one Chemical compound N=1CC(=O)N(CCCO)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 QADHJSLAOUPYKG-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
125000003342 alkenyl group Chemical group 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
125000004414 alkyl thio group Chemical group 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
230000001773 anti-convulsant effect Effects 0.000 description 1
125000003710 aryl alkyl group Chemical group 0.000 description 1
229960005070 ascorbic acid Drugs 0.000 description 1
235000010323 ascorbic acid Nutrition 0.000 description 1
239000011668 ascorbic acid Substances 0.000 description 1
239000002585 base Substances 0.000 description 1
229940049706 benzodiazepine Drugs 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
239000002775 capsule Substances 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
238000007865 diluting Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
230000004992 fission Effects 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
229940093915 gynecological organic acid Drugs 0.000 description 1
125000002768 hydroxyalkyl group Chemical group 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
150000002485 inorganic esters Chemical class 0.000 description 1
239000011630 iodine Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
229940098895 maleic acid Drugs 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
239000003158 myorelaxant agent Substances 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
239000000932 sedative agent Substances 0.000 description 1
230000001624 sedative effect Effects 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
239000000243 solution Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
238000010792 warming Methods 0.000 description 1

Classifications

- 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

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

NO159320A 1964-08-13 1965-08-12 NO118914B (fi)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US38946964A	1964-08-13	1964-08-13
US474159A US3391138A (en)	1964-08-13	1965-07-22	Certain 1-substituted-benzodiazepin-2-one compounds

Publications (1)

Publication Number	Publication Date
NO118914B true NO118914B (fi)	1970-03-02

Family

ID=27012718

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
NO159321A NO119588B (fi)	1964-08-13	1965-08-12
NO159320A NO118914B (fi)	1964-08-13	1965-08-12

Family Applications Before (1)

Application Number	Title	Priority Date	Filing Date
NO159321A NO119588B (fi)	1964-08-13	1965-08-12

Country Status (12)

Country	Link
US (1)	US3391138A (fi)
BE (2)	BE668188A (fi)
BR (2)	BR6571654D0 (fi)
CH (1)	CH462831A (fi)
DE (2)	DE1545952C3 (fi)
DK (2)	DK125554B (fi)
FR (1)	FR135F (fi)
GB (2)	GB1106040A (fi)
IL (2)	IL23999A (fi)
NL (2)	NL6510539A (fi)
NO (2)	NO119588B (fi)
SE (2)	SE310687B (fi)

Families Citing this family (18)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IL33961A (en) *	1969-03-13	1973-03-30	Sparamedica Ag	Benzodiazepine aminoalkyl carboxylates,their preparation and pharmaceutical compositions containing them
US3989829A (en) *	1969-04-18	1976-11-02	Sumitomo Chemical Company, Limited	1,4-Benzodiazepines
USRE28972E (en) *	1969-07-10	1976-09-21	Boehringer Ingelheim Gmbh	5-Aryl-1H-1,5-benzodiazepine-2,4-diones
US3867372A (en) *	1970-02-03	1975-02-18	Sumitomo Chemical Co	Benzodiazepine process
US3691157A (en) *	1970-08-12	1972-09-12	Rodney Ian Fryer	Preparation of 7-substituted-1-(2-diethylaminoethyl)-5-(2-halophenyl)-1,3-dihydro-2h-1,4-benzodiazepin-2-ones
DE2141904B2 (de) *	1970-08-31	1976-07-01	Sumitomo Chemical Co., Ltd., Osaka (Japan)	L- eckige klammer auf beta- (alpha'-tetrahydropyranyloxy)-aethyl eckige klammer zu -1,3-dihydro-5- phenyl-2h-1,4-benzodiazepin-2-one
AT314541B (de) *	1970-10-19	1974-04-10	Sumitomo Chemical Co	Verfahren zur Herstellung von neuen Benzodiazepinen und ihren Salzen
US4065451A (en) *	1971-03-30	1977-12-27	American Home Products	1,3-Dihydro-3-hydroxy-5-phenyl-2H-1,4-benzodiazepin-2-one, substituted diamino acetate esters and their acid salts
US3886276A (en) *	1971-03-30	1975-05-27	American Home Prod	1,3-Dihydro-3 -hydroxy-5-phenyl-2H-1,4-benzodiazepin-2-one, substituted diamino acetate esters and their acid salts in compositions and methods for inducing a calming effect
US3872089A (en) *	1971-05-14	1975-03-18	Hoffmann La Roche	Substituted thienodiazepines
US3966943A (en) *	1971-09-13	1976-06-29	The Upjohn Company	6-Pyridyl benzodiazepines antidepressants
US3926952A (en) *	1972-10-03	1975-12-16	American Home Prod	1,4-Benzodiazepin-2-ones and their synthesis
US4012413A (en) *	1973-05-17	1977-03-15	The Upjohn Company	Organic compounds and process
US3865815A (en) *	1973-11-29	1975-02-11	Hoffmann La Roche	7-Hydroxyamino-1,4-benzodiazepines
US4006135A (en) *	1974-06-19	1977-02-01	Ddsa Pharmaceuticals	Hydroxymethyl benzodiazepine derivatives
US3969504A (en) *	1975-02-14	1976-07-13	The Upjohn Co.	6-Phenyl benzodiazepine antidepressants
FI783743A (fi) *	1977-12-14	1979-06-15	Gerot Pharmazeutika	Foerfarande foer framstaellning av 3-di-n-propyl-acetoxi-benzodiazepin-2-oner
AT361492B (de) *	1978-12-18	1981-03-10	Gerot Pharmazeutika	Verfahren zur herstellung von neuen 3-hydroxy- 1,4-benzodiazepin-2-onen

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3236838A (en) *	1964-06-09	1966-02-22	Hoffmann La Roche	Certain 1-substituted-benzodiazepin-2-one compounds

0
- FR FR135D patent/FR135F/fr active Active
1965
- 1965-07-21 IL IL23999A patent/IL23999A/en unknown
- 1965-07-21 IL IL23998A patent/IL23998A/xx unknown
- 1965-07-22 US US474159A patent/US3391138A/en not_active Expired - Lifetime
- 1965-07-23 CH CH1036865A patent/CH462831A/de unknown
- 1965-07-27 DE DE1545952A patent/DE1545952C3/de not_active Expired
- 1965-07-29 DE DE19651545953 patent/DE1545953A1/de active Pending
- 1965-07-29 BR BR171654/65A patent/BR6571654D0/pt unknown
- 1965-07-29 BR BR171653/65A patent/BR6571653D0/pt unknown
- 1965-08-09 GB GB44504/67A patent/GB1106040A/en not_active Expired
- 1965-08-09 GB GB33994/65A patent/GB1102934A/en not_active Expired
- 1965-08-11 DK DK411365AA patent/DK125554B/da unknown
- 1965-08-11 DK DK411265AA patent/DK120848B/da unknown
- 1965-08-12 NL NL6510539A patent/NL6510539A/xx unknown
- 1965-08-12 BE BE668188D patent/BE668188A/xx unknown
- 1965-08-12 BE BE668189D patent/BE668189A/xx unknown
- 1965-08-12 NO NO159321A patent/NO119588B/no unknown
- 1965-08-12 NO NO159320A patent/NO118914B/no unknown
- 1965-08-12 NL NL6510538A patent/NL6510538A/xx unknown
- 1965-08-13 SE SE10628/65A patent/SE310687B/xx unknown
- 1965-08-13 SE SE10629/65A patent/SE312558B/xx unknown

Also Published As

Publication number	Publication date
GB1106040A (en)	1968-03-13
SE310687B (fi)	1969-05-12
NL6510538A (fi)	1966-02-14
IL23999A (en)	1969-05-28
DE1545953A1 (de)	1969-11-20
NO119588B (fi)	1970-06-08
DK120848B (da)	1971-07-26
SE312558B (fi)	1969-07-21
DK125554B (da)	1973-03-05
BE668188A (fi)	1966-02-14
US3391138A (en)	1968-07-02
CH462831A (de)	1968-09-30
NL6510539A (fi)	1966-02-14
FR135F (fi)
BR6571654D0 (pt)	1973-08-14
BR6571653D0 (pt)	1973-08-14
IL23998A (en)	1969-02-27
DE1545952B2 (de)	1974-07-04
DE1545952C3 (de)	1975-03-06
BE668189A (fi)	1965-12-01
GB1102934A (en)	1968-02-14
DE1545952A1 (de)	1969-12-18

Publication	Publication Date	Title
NO118914B (fi)	1970-03-02
IL22869A (en)	1968-11-27	A benzodiazepine derivative and process for the manufacture thereof
Sasaki et al.	1971	Heteroaromaticity. XLIX. Tetrazolo-azido isomerization in heteroaromatics. I. Syntheses and reactivities of some tetrazolopolyazines
SU523639A3 (ru)	1976-07-30	Способ получени производных диазепина
US3394143A (en)	1968-07-23	Heterocycleethanols
NO117366B (fi)	1969-08-04
US3557095A (en)	1971-01-19	Pyrazolodiazepinone compounds
SU430552A1 (ru)	1974-05-30	Способ получения производных бензодиазепина
AT256114B (de)	1967-08-10	Verfahren zur Herstellung von neuen Benzodiazepinderivaten
US4260773A (en)	1981-04-07	Intermediates for triazolobenzazepines
US3479357A (en)	1969-11-18	(6 - phenylpyrimidine)mono/bis(1h - 1,2,3-triazole- 4,5-dicarboxylic acid) lower alkyl esters
Bertelli et al.	2000	1‐(1, 2, 3‐triazol‐4‐yl)‐benzimidazolones, a new series of heterocyclic derivatives
US3215694A (en)	1965-11-02	Quinazoline-z-carboxaldehydes, acids, intermediates and process
FUJII et al.	1983	Purines. XXIV. Methylation of N6-Alkoxyadenines and N6-Methyladenine
DE1695211A1 (de)	1971-03-18	Verfahren zur Herstellung von Benzodiazepin-Derivaten
US3364228A (en)	1968-01-16	3-hydroxymethyl-4-(indol-3-yl)-hexahydro-1h-azepines and method of preparation
NO123492B (fi)	1971-11-29
US4427589A (en)	1984-01-24	Pyrimido[4,5-d][2]benzazepines
US4548750A (en)	1985-10-22	Pyrimido[4,5-d][2]benzazepines useful as sedatives and anxiolytic agents
US4259503A (en)	1981-03-31	Triazole intermediates for triazolobenzazepines
NO123037B (fi)	1971-09-20
Makisumi	1964	The Claisen Rearrangement in Aromatic Heterocyclic Compounds. II. The Thermal Rearrangement of Allyl 4-Quinolyl Ethers
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