NO784094L - 3-di-n-propyl-acetoxy-benzodiazepin-2-oner og fremgangsmaate til deres fremstilling - Google Patents

3-di-n-propyl-acetoxy-benzodiazepin-2-oner og fremgangsmaate til deres fremstilling

Info

Publication number: NO784094L
Authority: NO; Norway
Prior art keywords: general formula; radical; solvent; halogen; analogous method
Prior art date: 1977-12-14

Application number

NO784094A

Other languages

English (en)

Norwegian (no)

Inventor

Ludwig Schlager

Original Assignee

Gerot Pharmazeutika

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.)

1977-12-14

Filing date

1978-12-06

Publication date

1979-06-15

1977-12-14 Priority claimed from AT893877A external-priority patent/AT359509B/de

1978-11-21 Priority claimed from AT831278A external-priority patent/AT358051B/de

1978-12-06 Application filed by Gerot Pharmazeutika filed Critical Gerot Pharmazeutika

1979-06-15 Publication of NO784094L publication Critical patent/NO784094L/no

Links

238000000034 method Methods 0.000 title claims description 18
238000002360 preparation method Methods 0.000 title claims description 3
NIJJYAXOARWZEE-UHFFFAOYSA-N Valproic acid Chemical compound CCCC(C(O)=O)CCC NIJJYAXOARWZEE-UHFFFAOYSA-N 0.000 claims description 12
150000001875 compounds Chemical class 0.000 claims description 12
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 8
238000006243 chemical reaction Methods 0.000 claims description 8
229910052739 hydrogen Inorganic materials 0.000 claims description 8
239000001257 hydrogen Substances 0.000 claims description 8
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
229910052736 halogen Inorganic materials 0.000 claims description 5
239000002904 solvent Substances 0.000 claims description 5
150000002367 halogens Chemical class 0.000 claims description 4
150000002431 hydrogen Chemical class 0.000 claims description 4
239000011877 solvent mixture Substances 0.000 claims description 4
150000003512 tertiary amines Chemical class 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
239000011230 binding agent Substances 0.000 claims description 3
230000015572 biosynthetic process Effects 0.000 claims description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
229910052801 chlorine Inorganic materials 0.000 claims description 2
125000001309 chloro group Chemical group Cl* 0.000 claims description 2
229910052757 nitrogen Inorganic materials 0.000 claims description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 1
150000008064 anhydrides Chemical class 0.000 claims 1
239000012442 inert solvent Substances 0.000 claims 1
150000002500 ions Chemical class 0.000 claims 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
239000002243 precursor Substances 0.000 claims 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
150000002148 esters Chemical class 0.000 description 8
238000004519 manufacturing process Methods 0.000 description 5
GYIUDLLQLVWKPP-UHFFFAOYSA-N 2-propylpentanoyl 2-propylpentanoate Chemical compound CCCC(CCC)C(=O)OC(=O)C(CCC)CCC GYIUDLLQLVWKPP-UHFFFAOYSA-N 0.000 description 4
PITHYUDHKJKJNQ-UHFFFAOYSA-N 2-propylpentanoyl chloride Chemical compound CCCC(C(Cl)=O)CCC PITHYUDHKJKJNQ-UHFFFAOYSA-N 0.000 description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
CWRVKFFCRWGWCS-UHFFFAOYSA-N Pentrazole Chemical compound C1CCCCC2=NN=NN21 CWRVKFFCRWGWCS-UHFFFAOYSA-N 0.000 description 4
239000000203 mixture Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
229960000604 valproic acid Drugs 0.000 description 4
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
230000001773 anti-convulsant effect Effects 0.000 description 3
239000000155 melt Substances 0.000 description 3
-1 oxazepam ester Chemical class 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
239000000243 solution Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
FERBACJQVQVCKH-UHFFFAOYSA-N 3-Hydroxy-N-desalkyl-2-Oxoquazepam Natural products C12=CC(Cl)=CC=C2NC(=O)C(O)N=C1C1=CC=CC=C1F FERBACJQVQVCKH-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
238000006972 Polonovski rearrangement reaction Methods 0.000 description 2
QRUFWTOCUCFKLZ-UHFFFAOYSA-N [7-chloro-5-(2-fluorophenyl)-2-oxo-1,3-dihydro-1,4-benzodiazepin-3-yl] 2-propylpentanoate Chemical compound C12=CC(Cl)=CC=C2NC(=O)C(OC(=O)C(CCC)CCC)N=C1C1=CC=CC=C1F QRUFWTOCUCFKLZ-UHFFFAOYSA-N 0.000 description 2
239000013078 crystal Substances 0.000 description 2
229940079593 drug Drugs 0.000 description 2
230000000694 effects Effects 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
230000007935 neutral effect Effects 0.000 description 2
229960004535 oxazepam Drugs 0.000 description 2
239000003208 petroleum Substances 0.000 description 2
239000000843 powder Substances 0.000 description 2
239000000047 product Substances 0.000 description 2
DIWRORZWFLOCLC-HNNXBMFYSA-N (3s)-7-chloro-5-(2-chlorophenyl)-3-hydroxy-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound N([C@H](C(NC1=CC=C(Cl)C=C11)=O)O)=C1C1=CC=CC=C1Cl DIWRORZWFLOCLC-HNNXBMFYSA-N 0.000 description 1
SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 description 1
CQQUWTMMFMJEFE-UHFFFAOYSA-N 2-chloro-n,n-diethylacetamide Chemical compound CCN(CC)C(=O)CCl CQQUWTMMFMJEFE-UHFFFAOYSA-N 0.000 description 1
XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
150000001204 N-oxides Chemical class 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
SEQDDYPDSLOBDC-UHFFFAOYSA-N Temazepam Chemical compound N=1C(O)C(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 SEQDDYPDSLOBDC-UHFFFAOYSA-N 0.000 description 1
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
230000001154 acute effect Effects 0.000 description 1
125000004423 acyloxy group Chemical group 0.000 description 1
239000001961 anticonvulsive agent Substances 0.000 description 1
229960003965 antiepileptics Drugs 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
YEJAJYAHJQIWNU-UHFFFAOYSA-N azelastine hydrochloride Chemical compound Cl.C1CN(C)CCCC1N1C(=O)C2=CC=CC=C2C(CC=2C=CC(Cl)=CC=2)=N1 YEJAJYAHJQIWNU-UHFFFAOYSA-N 0.000 description 1
229940049706 benzodiazepine Drugs 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
125000000068 chlorophenyl group Chemical group 0.000 description 1
239000000812 cholinergic antagonist Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
238000010908 decantation Methods 0.000 description 1
IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
239000003814 drug Substances 0.000 description 1
239000003480 eluent Substances 0.000 description 1
230000007717 exclusion Effects 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
239000005457 ice water Substances 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
229960004391 lorazepam Drugs 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
ADIMAYPTOBDMTL-UHFFFAOYSA-N oxazepam Chemical compound C12=CC(Cl)=CC=C2NC(=O)C(O)N=C1C1=CC=CC=C1 ADIMAYPTOBDMTL-UHFFFAOYSA-N 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
125000005547 pivalate group Chemical group 0.000 description 1
125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000012216 screening Methods 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
230000002048 spasmolytic effect Effects 0.000 description 1
238000010254 subcutaneous injection Methods 0.000 description 1
239000007929 subcutaneous injection Substances 0.000 description 1
150000003890 succinate salts Chemical class 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1
229960003188 temazepam Drugs 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
239000003204 tranquilizing agent Substances 0.000 description 1
230000002936 tranquilizing effect Effects 0.000 description 1
230000009466 transformation Effects 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Plural Heterocyclic Compounds (AREA)

NO784094A 1977-12-14 1978-12-06 3-di-n-propyl-acetoxy-benzodiazepin-2-oner og fremgangsmaate til deres fremstilling NO784094L (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
AT893877A AT359509B (de)	1977-12-14	1977-12-14	Verfahren zur herstellung von neuen 3-di-n- -propylacetoxybenzodiazepin-2-onen
AT831278A AT358051B (de)	1978-11-21	1978-11-21	Verfahren zur herstellung von neuen 3-di-n- -propyl-acetoxy-benzodiazepin-2-onen

Publications (1)

Publication Number	Publication Date
NO784094L true NO784094L (no)	1979-06-15

Family

ID=25604664

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO784094A NO784094L (no)	1977-12-14	1978-12-06	3-di-n-propyl-acetoxy-benzodiazepin-2-oner og fremgangsmaate til deres fremstilling

Country Status (20)

Country	Link
US (1)	US4261987A (xx)
JP (1)	JPS54138589A (xx)
AU (1)	AU4255778A (xx)
BG (2)	BG29284A3 (xx)
DD (1)	DD139851A5 (xx)
DE (1)	DE2852606A1 (xx)
DK (1)	DK562478A (xx)
ES (1)	ES475960A1 (xx)
FI (1)	FI783743A (xx)
FR (1)	FR2411836A1 (xx)
GB (1)	GB2010267A (xx)
GR (1)	GR65190B (xx)
IT (1)	IT1104583B (xx)
LU (1)	LU80632A1 (xx)
NL (1)	NL7812144A (xx)
NO (1)	NO784094L (xx)
PL (1)	PL114759B1 (xx)
RO (1)	RO79702A (xx)
SE (1)	SE7812649L (xx)
YU (1)	YU294378A (xx)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IT1190133B (it) *	1986-06-19	1988-02-10	Chiesi Farma Spa	Derivati di acido valproico e di acido (e)-2-valproenoico,procedimento per la loro preparazione e relative composizioni farmaceutiche
US5030632A (en) *	1986-09-23	1991-07-09	Sandoz Pharm. Corp.	Low dose temazepam
US5211954A (en) *	1986-09-23	1993-05-18	Sandoz Ltd.	Low dose temazepam
US5629310A (en) *	1986-09-23	1997-05-13	Sterling; William R.	Low dose temazepam

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3176009A (en) *		1965-03-30		Hydrolysis of l-acylated-j-acyloxy benzodiazepines
BE621819A (xx) *	1961-08-29
AT242706B (de) *	1962-11-28	1965-10-11	Hoffmann La Roche	Verfahren zur Herstellung von neuen Benzodiazepin-Derivaten
GB1051795A (xx) *	1964-02-11
US3236838A (en) *	1964-06-09	1966-02-22	Hoffmann La Roche	Certain 1-substituted-benzodiazepin-2-one compounds
FR135F (xx) *	1964-08-13
US3801568A (en) *	1972-02-07	1974-04-02	American Home Prod	Optically active 1,3-dihydro-3-substituted 5-phenyl-2h-1,4-benzodiazepin-2-ones and process for their separation
FR2269349B1 (xx) *	1974-04-30	1979-03-16	Ferrer Labor

1978
- 1978-12-05 FI FI783743A patent/FI783743A/fi unknown
- 1978-12-05 DE DE19782852606 patent/DE2852606A1/de not_active Withdrawn
- 1978-12-06 GR GR57804A patent/GR65190B/el unknown
- 1978-12-06 NO NO784094A patent/NO784094L/no unknown
- 1978-12-08 SE SE7812649A patent/SE7812649L/xx unknown
- 1978-12-08 LU LU80632A patent/LU80632A1/de unknown
- 1978-12-12 FR FR7834868A patent/FR2411836A1/fr not_active Withdrawn
- 1978-12-12 BG BG784170A patent/BG29284A3/xx unknown
- 1978-12-12 BG BG7944352A patent/BG29285A3/xx unknown
- 1978-12-12 PL PL1978211668A patent/PL114759B1/pl unknown
- 1978-12-12 GB GB7848060A patent/GB2010267A/en not_active Withdrawn
- 1978-12-13 ES ES475960A patent/ES475960A1/es not_active Expired
- 1978-12-13 NL NL7812144A patent/NL7812144A/xx not_active Application Discontinuation
- 1978-12-13 IT IT7830778A patent/IT1104583B/it active
- 1978-12-13 DD DD78209726A patent/DD139851A5/de unknown
- 1978-12-14 DK DK562478A patent/DK562478A/da unknown
- 1978-12-14 JP JP15565978A patent/JPS54138589A/ja active Pending
- 1978-12-14 RO RO78101144A patent/RO79702A/ro unknown
- 1978-12-14 YU YU02943/78A patent/YU294378A/xx unknown
- 1978-12-14 AU AU42557/78A patent/AU4255778A/en active Pending
- 1978-12-14 US US05/970,057 patent/US4261987A/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
FR2411836A1 (fr)	1979-07-13
SE7812649L (sv)	1979-06-15
GB2010267B (xx)
YU294378A (en)	1983-06-30
NL7812144A (nl)	1979-06-18
PL211668A1 (pl)	1979-07-30
LU80632A1 (de)	1979-04-09
BG29285A3 (en)	1980-10-15
GR65190B (en)	1980-07-29
DE2852606A1 (de)	1979-06-21
PL114759B1 (en)	1981-02-28
DK562478A (da)	1979-06-15
RO79702A (ro)	1982-08-17
FI783743A (fi)	1979-06-15
US4261987A (en)	1981-04-14
DD139851A5 (de)	1980-01-23
GB2010267A (en)	1979-06-27
IT1104583B (it)	1985-10-21
BG29284A3 (en)	1980-10-15
JPS54138589A (en)	1979-10-27
ES475960A1 (es)	1979-05-01
AU4255778A (en)	1979-06-21
IT7830778A0 (it)	1978-12-13

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US3989689A (en)	1976-11-02	4-Carbamoyl-1-benzazepines