IE33991B1 - Benzodiazepine derivatives - Google Patents
Benzodiazepine derivativesInfo
- Publication number
- IE33991B1 IE33991B1 IE618/73A IE61870A IE33991B1 IE 33991 B1 IE33991 B1 IE 33991B1 IE 618/73 A IE618/73 A IE 618/73A IE 61870 A IE61870 A IE 61870A IE 33991 B1 IE33991 B1 IE 33991B1
- Authority
- IE
- Ireland
- Prior art keywords
- compound
- formula
- alkoxyalkoxy
- alkoxy
- alkyl
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/22—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/12—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
- C07K1/006—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length of peptides containing derivatised side chain amino acids
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Analytical Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
Abstract
1306451 Benzodiazepines F HOFFMANNLA ROCHE & CO AG 11 Feb 1970 [14 Feb 1969] 6450/70 Heading C2C Compounds of the general Formula (I) (R 1 =halogen, NO 2 ; R 2 = Ph, Py, halophenyl; R 3 = H, alkyl, hydroxyalkyl, acyloxyalkyl, haloalkyl, carbalkoxy, alkylaminoalkyl, dialkylaminoalkyl; R 4 = alkoxy, haloalkoxy, alkylaminoalkoxy, dialkylaminoalkoxy, hydroxyalkoxy, alkoxyalkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl; R 5 = H, OH; R 6 = H, carbalkoxy), their 4-oxides (R 5,6 = H) and salts are prepared by (a) reacting a compound of the Formula (II) or 4-oxide thereof with R 7 R 8 CHX (R 7 =H, alkyl, haloalkyl, carbalkoxy, acyloxyalkyl ; R8 = alkoxy, haloalkoxy, alkylthio, alkoxyalkoxy; X=halogen, leaving group), (b) reacting (II), R 6 =H, with an alkyl vinyl ether, (c) reacting a compound of the Formula (VI) (R 10 = H, alkyl, hydroxyalkyl, haloalkyl, alkylaminoalkyl, dialkylaminoalkyl, acyloxyalkyl; R 11 =R 4 , but at least one of R 10,11 =monohaloalkyl or monohaloalkoxy) or 4-oxide thereof with an alkylamine or dialkylamine, (d) alkylating a compound of the Formula (VII) (R 12 = alkoxy, alkylaminoalkoxy, dialkylaminoalkoxy, alkoxyalkoxy, alkylthio, aminoalkoxy; R 13 =H, alkyl, alkylaminoalkyl, dialkylaminoalkyl, aminoalkyl, but at least one of R 12,13 = aminoalkoxy, alkylaminoalkoxy, aminoalkyl or alkylaminoalkyl) or 4-oxide thereof, (e) removing the protecting group from a compound of the Formula (VIII) (R 14 = alkoxy, alkylaminoalkoxy, dialkylaminoalkoxy, alkoxyalkoxy, alkylthio, protected alkylaminoalkoxy; R 15 = H, alkyl, alkylaminoalkyl, dialkylaminoalkyl, acyloxyalkyl, protected alkylaminoalkyl, but at least one of R 14,15 = protected group) or 4-oxide thereof, (f) replacing the aliphatically bound halogen atom(s) by OH in a compound of the Formula (IX) (R 16 = alkoxy, haloalkoxy, alkylaminoalkoxy, dialkylaminoalkoxy, hydroxyalkoxy, alkoxyalkoxy, alkylthio; R 17 =H, alky], hydroxyalkyl, haloalkyl, carbalkoxy, alkylaminoalkyl, dialkylaminoalkyl, acyloxyalkyl, but at least one of R 16,17 = monehaloalkyl or monohaloalkoxy) or 4-oxide thereof, (g) oxidizing a compound of the Formula (X) (R 18 = alkylthio; R 19 = H, alkyl, hydroxyalkyl, haloalkyl, carbalkoxy, acyloxyalkyl) or 4- oxide thereof, (h) cyclizing a compound of the Formula (XI) (i) hydrolysing a compound of the Formula (XII) (R 20 = acyl), (j) deoxygenating a compound of the Formula (XIII) (R 21 = alkoxy, haloalkoxy, alkylaminoalkoxy, dialkylaminoalkoxy, hydroxyalkoxy, alkoxyalkoxy, alkylthio), (k) dehydrating a compound of the Formula (XIV) (R 22 = alkoxy, alkoxyalkoxy, dialkylaminoalkoxy; R 23 =H, alkyl, carbalkoxy, dialkylaminoalkyl, acyloxyalkyl, (1) oxidizing or dehydrogenating a compound of the Formula (XV) (B 24 =alkoxy, alkylaminoalkoxy, dialkylaminoalkoxy, hydroxyalkoxy, alkoxyalkoxy; R 25 =H, alkyl, hydroxyalkyl, carbalkoxy, alkylaminoalkyl, dialkylaminoalkyl, acyloxyalkyl), (m) saponifying and decarboxylating a compound of the Formula (XVI) (R 26 = alkyl; R 27 = H, alkyl, hydroxyalkyl, haloalkyl, alkylaminoalkyl, dialkylaminoalkyl, acyloxyalkyl), (n) oxidizing a compound of the Formula (XVII) to the 3-hydroxy compound, (o) converting a compound of the Formula (XVIII) (R 28 = acyl; R 29 = alkoxy, alkylaminoalkoxy, dialkylaminoalkoxy, hydroxyalkoxy, alkoxyalkoxy) with a base into the corresponding 4,5- dehydro compound, (p) converting a compound of the Formula (XIX) (R 30 =mesyl, tosyl; R 31 =H, alkyl, hydroxyalkyl, carbalkoxy, dialkylaminoalkyl, acyloxyalkyl ; R 32 = alkoxy, dialkylaminoalkoxy, hydroxyalkoxy, alkoxyalkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl) with a strong base into the corresponding 4,5-dehydro compound, (q) rearranging the corresponding 3,4-dehydro compound, (r) acylating a compound of the Formula (XXI) (R 40 = hydroxyalkyl ; R 41 = alkoxy, haloalkoxy, dialkylaminoalkoxy, alkoxyalkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl) or 4-oxide thereof, or (s) replacing the aliphatically bound halogen atom by an acyloxy group in a compound of the Formula (XXII) (R 42 haloalkyl; R 43 = alkoxy, dialkylaminoalkoxy, alkoxyalkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl) or 4-oxide thereof, optionally followed in each case by salt formation. The above compounds are anticonvulsants, muscle relaxants, sedatives and anxiolytics, and may be administered in the form of pharmaceutical preparations containing them in association with a carrier.
[GB1306451A]
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH225569A CH562220A5 (en) | 1969-02-14 | 1969-02-14 |
Publications (1)
Publication Number | Publication Date |
---|---|
IE33991B1 true IE33991B1 (en) | 1974-12-30 |
Family
ID=4229492
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
IE156/70A IE33988B1 (en) | 1969-02-14 | 1970-02-06 | Benzodiazepine derivatives and the manufacture thereof |
IE618/73A IE33991B1 (en) | 1969-02-14 | 1970-02-06 | Benzodiazepine derivatives |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
IE156/70A IE33988B1 (en) | 1969-02-14 | 1970-02-06 | Benzodiazepine derivatives and the manufacture thereof |
Country Status (23)
Country | Link |
---|---|
AT (10) | AT301555B (en) |
BE (1) | BE745852A (en) |
BR (1) | BR6915093D0 (en) |
CA (1) | CA971960A (en) |
CH (1) | CH562220A5 (en) |
CS (1) | CS159260B2 (en) |
DE (1) | DE2005508A1 (en) |
DK (1) | DK137899B (en) |
DO (1) | DOP1970001703A (en) |
ES (1) | ES376528A1 (en) |
FI (1) | FI49965C (en) |
FR (1) | FR2034550B1 (en) |
GB (5) | GB1306454A (en) |
IE (2) | IE33988B1 (en) |
IL (2) | IL33821A (en) |
IS (1) | IS1906A7 (en) |
NL (1) | NL156401B (en) |
NO (2) | NO128328B (en) |
OA (1) | OA03435A (en) |
PL (1) | PL80826B1 (en) |
RO (5) | RO58075A (en) |
SE (1) | SE358393B (en) |
SU (11) | SU453841A3 (en) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BE787117A (en) * | 1971-08-04 | 1973-02-05 | Hoffmann La Roche | BENZODIAZEPINE DERIVATIVES |
JPS4867288A (en) * | 1971-12-14 | 1973-09-13 | ||
US3932637A (en) * | 1974-07-22 | 1976-01-13 | Sumitomo Chemical Company, Limited | Methods and compositions for improving the feed intake of meat producing animals |
CA1163266A (en) * | 1980-07-31 | 1984-03-06 | Albert E. Fischli | Benzodiazepine derivatives |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3136815A (en) * | 1959-12-10 | 1964-06-09 | Hoffmann La Roche | Amino substituted benzophenone oximes and derivatives thereof |
-
1969
- 1969-02-14 CH CH225569A patent/CH562220A5/xx not_active IP Right Cessation
- 1969-12-15 BR BR215093/69A patent/BR6915093D0/en unknown
-
1970
- 1970-02-02 IL IL33821A patent/IL33821A/en unknown
- 1970-02-04 CA CA073,934A patent/CA971960A/en not_active Expired
- 1970-02-05 OA OA53847A patent/OA03435A/en unknown
- 1970-02-06 IE IE156/70A patent/IE33988B1/en unknown
- 1970-02-06 IE IE618/73A patent/IE33991B1/en unknown
- 1970-02-06 DE DE19702005508 patent/DE2005508A1/en not_active Ceased
- 1970-02-10 SU SU1691948A patent/SU453841A3/en active
- 1970-02-10 SU SU1666627A patent/SU428603A3/en active
- 1970-02-10 SU SU1691943A patent/SU404253A3/ru active
- 1970-02-10 SU SU1658463A patent/SU406359A3/ru active
- 1970-02-10 SU SU1691947A patent/SU406360A3/ru active
- 1970-02-10 SU SU1691525A patent/SU415880A3/en active
- 1970-02-10 SU SU1665719A patent/SU431673A3/ru active
- 1970-02-10 SU SU1691526A patent/SU421195A3/en active
- 1970-02-10 SU SU1691944A patent/SU402219A3/ru active
- 1970-02-10 SU SU1400104A patent/SU497774A3/en active
- 1970-02-11 GB GB6675372A patent/GB1306454A/en not_active Expired
- 1970-02-11 CS CS95470*#A patent/CS159260B2/cs unknown
- 1970-02-11 GB GB645070A patent/GB1306451A/en not_active Expired
- 1970-02-11 GB GB4314272A patent/GB1306455A/en not_active Expired
- 1970-02-11 GB GB3375172A patent/GB1306452A/en not_active Expired
- 1970-02-12 IS IS1906A patent/IS1906A7/en unknown
- 1970-02-12 BE BE745852D patent/BE745852A/en unknown
- 1970-02-12 DO DO1970001703A patent/DOP1970001703A/en unknown
- 1970-02-13 SE SE01893/70A patent/SE358393B/xx unknown
- 1970-02-13 AT AT505071A patent/AT301555B/en not_active Expired
- 1970-02-13 AT AT505571A patent/AT302321B/en not_active IP Right Cessation
- 1970-02-13 AT AT505171A patent/AT302317B/en not_active IP Right Cessation
- 1970-02-13 AT AT505671A patent/AT302322B/en not_active IP Right Cessation
- 1970-02-13 NO NO00510/70A patent/NO128328B/no unknown
- 1970-02-13 DK DK72870AA patent/DK137899B/en not_active Application Discontinuation
- 1970-02-13 NL NL7002084.A patent/NL156401B/en not_active IP Right Cessation
- 1970-02-13 ES ES376528A patent/ES376528A1/en not_active Expired
- 1970-02-13 FI FI700400A patent/FI49965C/en active
- 1970-02-13 AT AT504971A patent/AT302316B/en not_active IP Right Cessation
- 1970-02-13 AT AT505771A patent/AT302323B/en not_active IP Right Cessation
- 1970-02-13 AT AT505471A patent/AT302320B/en not_active IP Right Cessation
- 1970-02-13 AT AT505271A patent/AT302318B/en not_active IP Right Cessation
- 1970-02-13 AT AT131770A patent/AT299208B/en not_active IP Right Cessation
- 1970-02-13 PL PL1970138780A patent/PL80826B1/en unknown
- 1970-02-13 FR FR707005175A patent/FR2034550B1/fr not_active Expired
- 1970-02-13 AT AT505371A patent/AT302319B/en not_active IP Right Cessation
- 1970-02-14 RO RO62467A patent/RO58075A/ro unknown
- 1970-02-14 RO RO68268A patent/RO57030A/ro unknown
- 1970-02-14 RO RO68266A patent/RO57160A/ro unknown
- 1970-02-14 RO RO68269A patent/RO57161A/ro unknown
- 1970-02-14 RO RO68267A patent/RO57028A/ro unknown
- 1970-05-12 GB GB3385272A patent/GB1306453A/en not_active Expired
-
1971
- 1971-05-13 SU SU1657960A patent/SU517258A3/en active
-
1973
- 1973-01-24 NO NO00292/73A patent/NO128110B/no unknown
- 1973-05-22 IL IL7342330A patent/IL42330A0/en unknown
Also Published As
Similar Documents
Publication | Publication Date | Title |
---|---|---|
YU56995A (en) | ONLY DERIVED INDOLA | |
AR010307A1 (en) | DERIVED FROM ERYTHROMYCIN A, PHARMACEUTICAL COMPOSITION AND ANTIBACTERIAL PREPARATION CONTAINING IT. | |
EP0749305A4 (en) | Process for making avermectin/zein compositions | |
FR2390446A1 (en) | NEW TRIAZINES 1,3,5-S-HEXAHYDROTRISUBSTITUESES, THEIR PREPARATION AND THEIR APPLICATION TO THE FIGHT AGAINST MICROBIAL DEVELOPMENT | |
IE33991B1 (en) | Benzodiazepine derivatives | |
MY120550A (en) | Substituted 1,2,3,4,5,6-hexahydro-2,6-methano-3-benzazocin-10-ols, processes for preparing them and their use as pharmaceutical compositions. | |
CA2174707A1 (en) | Chromone derivatives as nk1 and substance p antagonists | |
ES8300320A1 (en) | Zinc retinoate, its preparation and the topic compositions containing it. | |
JPS5419969A (en) | Proline derivative and its preparation | |
ES8403911A1 (en) | 3,6-dianhydro-hexite mononitrates, processes for their preparation and pharmaceutical preparations. | |
FR2417495A1 (en) | METAL SALTS OF MONO- AND DINITRODIHYDROXYDIAZOBENZENE, THEIR OBTAINING AND THEIR APPLICATION AS INITIAL EXPLOSIVES IN IGNITION AND PRIMING CHARGES | |
JPS5716852A (en) | Nitrile derivative, its preparation, and fibrosis suppressing agent containing the same | |
JPS5424882A (en) | Novel heterocyclic compounds and their preparation | |
ES452772A1 (en) | Novel dibenzopyran and its preparation | |
JPS5432471A (en) | 8-aklyl-3-oxo-2-oxabicyclo(3,2,1)-octanes, their preparation, and perfume composition containing the same | |
ES8107222A1 (en) | 17-Cycloalkylmethyl-6-methylene-morphinane-derivatives. | |
JPS5419945A (en) | Cyclohexane derivatives, their preparation and herbicides | |
FR2377406A1 (en) | TETRATHIAPENTALENE AND TETRASELENAPENTALENE COMPOUNDS | |
ES8303297A1 (en) | New peptide, process for preparation thereof and use thereof. | |
JPS547427A (en) | Novel disazo compounds and their preparation | |
JPS5315344A (en) | Preparation of 5-cyclohexadecene-1-one | |
JPS53133229A (en) | Novel disazo compounds and their preparation | |
JPS5412355A (en) | Alkyl cyclohexyldichlorosilane compounds and their preparation | |
JPS55108883A (en) | Ethyl-(gamma-acetamino-gamma-ethoxycarbonyl-gamma-cyanopropyl- methyl) phosphinate and its preparation | |
JPS5716885A (en) | 3,4-benzo-7-thia-2-azabicyclo 3,3,1 nonane derivative |