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IL42720A - 5-phenyl-1,3-dihydro-3-aminomethylene-2h-1,4-benzodiazepin 2-one derivatives,their preparation and pharmaceutical compositions containing them - Google Patents

5-phenyl-1,3-dihydro-3-aminomethylene-2h-1,4-benzodiazepin 2-one derivatives,their preparation and pharmaceutical compositions containing them

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Publication number
IL42720A
IL42720A IL42720A IL4272073A IL42720A IL 42720 A IL42720 A IL 42720A IL 42720 A IL42720 A IL 42720A IL 4272073 A IL4272073 A IL 4272073A IL 42720 A IL42720 A IL 42720A
Authority
IL
Israel
Prior art keywords
formula
group
compound
effected
reaction
Prior art date
Application number
IL42720A
Other versions
IL42720A0 (en
Original Assignee
Thomae Gmbh Dr K
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.)
Filing date
Publication date
Priority claimed from DE19722234150 external-priority patent/DE2234150A1/en
Priority claimed from DE2324962A external-priority patent/DE2324962A1/en
Priority claimed from DE19732326657 external-priority patent/DE2326657A1/en
Application filed by Thomae Gmbh Dr K filed Critical Thomae Gmbh Dr K
Publication of IL42720A0 publication Critical patent/IL42720A0/en
Publication of IL42720A publication Critical patent/IL42720A/en

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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

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

Claims (3)

42720/2
1. Compounds of general formula (wherein R^ and R2 , which may be the same or differen , each represents a hydrogen atom; a straight- or branched-chain alk l group containing from 1 to 5 carbon atoms, optionally substituted by a furyl, dialkylamino , hydroxy, carbalkoxy, aminocarbonyl or moxpholinocarbonyl group a straight or branched alkenyl group of 2 to 5 carbon atoms, a cycloalkyl or a phenyl group; or R^ and together with the nitrogen atom to which they are attached represent a pyrrolidino,piperidino, hexamethyleneimino, morpholino, thio-morpholino, thiomorpholine-S-oxido or N-alkyl-piperazino group R3 represents a halogen atom or a nitro or trifluoromethyl group; represents a hydrogen atom, a halogen atom or a trifluoromethyl group; and R_ represents a hydrogen atom, or an alkyl, cycloalkylmethyl , alkylaminoalkyl , dialkylaminoalkyl , or trifluoromethylalkyl group) and acid addition salts thereof.
2. Compounds of general formula I as claimed in claim 1, except for those wherein and together with the nitrogen atom to which they are attached represent a thiomopholine-S-oxido group and acid addition salts thereof..
3. Compounds of general formula I wherein and which may be the same or different, each represents a hydrogen atom, or a straight- or branched-chain alkyl group with from 1 to 3 carbon atoms , or and together with the nitrogen atom to which they are attached represent a morpholino group, R^ and R^ represent halogen atoms and R^ represents a hydrogen atom or an alkyl group with 1 to 3 carbon atoms and physiologically compatible acid addition salts thereof.
4. Compounds of general formula I wherein R^ and R^, which may be the same or different, each represents a hydrogen atom or a methyl or ethyl group, or R^ and R2 together with the nitrogen atom to which they are attached represent a morpholino, thiomorpholino or thiomorpholine-S-oxide group, represents a fluorine, bromine or iodine atom, or a nitro group, represents a hydrogen, fluorine or chlorine atom, and represents a hydrogen atom, or a methyl, ethyl or 2 ,2 ,2-trifluoroethyl group and physiologically compatible acid addition salts thereof.
5. 7-Chloro-5-(2-chlorophenyl)-l ,3-dihydro-l-methyl -3-(morpholino-methylene)-2H-l ,4-benzodiazepine-2-one and physiologically compatible acid addition salts.
6. 3- (Amino-methy1ene)-7-chloro-5-(2-chloropheny\) - 1 ,3-dihydro-2H-l ,4-benzodiazepine-2-one and physiologically compatible acid addition salts thereof.
7. 3-(Ethylamino-methylene) -7-chloro- 5- ( 2-chlorophenyl) -1 ,3-dihydro-l-methyl-2H-l ,4-benzodiazepine-2-one and physiologically compatible acid addition salts thereof.
8. -Bromo- 5- ( 2-chlorophenyl) -1 ,3-dihydro-l-methy1-3-(morpho1ino-methylene)-2H-l,4-benzodiaze ine-2-one and physiologically compatible acid addition salts thereof.
9. 3- (Amino-methylene) -7-bromo- 5- ( 2-chlorophenyl) -1 ,3-dihydro-l-methyl-2H-l ,4-benzodiazepine-2-one and physiologically compatible acid addition salts thereof.
10. 3- ( Amino-methylene) -7-bromo- 5- ( 2-chloropheny1) - 1 ,3-dihydro-2H-l , 4-benzodiazepine-2-one and physiologically compatible acid addition salts thereof.
11. 3- (Ethylamino-methy1ene) - 7-bromo- 5- ( 2-chloropheny1) -1 ,3-dihydro-2H- 1 ,4-benzodiazepine-2-one and physiologically compatible acid addition salts thereof.
12. 3- (Amino-methylene) -5- ( 2-chlorophenyl)-l, 3-dihydro-7-iodo-l-methyl-2H-l ,4-benzodiazepine-2-one and physiologically compatible acid addition salts thereof.
13. Compounds as claimed in claim 1 except for those claimed in claims 5 to 12 as herein specifically disclosed.
14. A process for the preparation of compounds of (wherein and which may be the same or different, each represents a straight- or branched-chain alkyl -Θ*· alkcnyl group containing from 1 to 5 carbon atoms , 42720/2 a straight or branched chain alkenyl group of 2 to 5 carbon optionally substituted by a furyl or dialkylamino/ or a atoms cycloalkyl or phenyl group, or R^ and together with the nitrogen atom to which they are attached, represent a pyrrolidino, piperidino , hexamethyleneimino , morpholino, thiomorpholino or N-alkyl-piperazino group, and , R^ and R-. are as defined in claim 1) which comprises reacting a (wherein R »R, and R_ are as defined in claim 1) with a compound of formula R^ 0 > CH N (wherein R^ and R^, which may be the -same of different, each represents a straight- or branched-chain alkyl', ;.' ~ ' group containing from 1 to 5 carbon atoms , optionally substituted by a furyl or dialkylamino group, a straight or branched chain alkenyl group of 2 to 5 carbon atoms , > or R and together with the nitrogen atom to which they are attached, represent a pyrrolidino, piperidino , hexamethyleneimino , morpholino, thiomorpholino or N-alkyl-piperazino group, and the groups R∑. represent lower alkyl groups).
15. A process as claimed in claim 14 wherein the reaction is carried out in the absence of moisture.
16. A process as claimed in claim 14 or claim 15 wherein the reaction is effected in the presence of a solvent.
17. A process as claimed in claim 16 wherein the solvent comprises tetrahydrofuran, dioxan, dimethylformamide , or ethylene glycol dimethyl ether.
18. A process as claimed in claim 14 or claim 15 wherein the reaction is effected in the presence of an excess of the compound of formula III used which excess acts as solvent.
19. A process as claimed in claim 14 or claim 15 wherein the reaction is effected in the absence of a solvent.
20. A process as claimed in any of claims 14 to 19 wherein the reaction is effected at temperatures of from 20 to 220°C. 42720/2
21. A process as claimed in claim 20 wherein the reaction is effected at temperatures of from 80 to 140°C.
22. A process as claimed in any of claims 14 to 21 wherein a compound of formula II is used wherein R,_ represents a hydrogen atom and heating is continued for 10 to 70 hours whereby a compound of formula I wherein R5 represents a lower alkyl group is produced.
23. A process for the preparation of compounds of general formula I (wherein R± and R2> which may be the same or different, each represents a straight- or branched-chain alkyl .group containing from 1 to 5 carbon atoms; a straight or branched alkenyl group of 2 to 5 carbon atoms, a cycloalkyl or phenyl group; 'or R± and R2 together with the nitrogen atom to which they are attached represent a pyrrolidino, piperidino, hexamethyleneimino , morpholino, thiomorpholino or N-alkyl-piperazino group; and R3, R4j and R5 are as defined i Claim 1) which comprises reacting a compound of the formula (wherein R , R, and Rc are as defined in claim 1) with a J 4 o compound of formula X R» \ ^ 1 (wherein R" and R! , which may be the same or different, each represents a straight- or branched-chain alkyl or alkenyl group containing from 1 to 5 carbon atoms; or a cycloalkyl or phenyl group; or R1^ and R^ together with the nitrogen atom to which they are attached represent a pyrrolidino, piperidino, hexamethyleneimino , morpholino, thiomorpholino or N-alkyl-piperazino group; and the radicals X either both represent groups of the formula N , or one of the radicals represents a group of the formula ORj. (wherein Rj. is as defined in claim 14) and the other represents a group of the formula R II 2
24. A process as claimed in claim 23 wherein the reaction is carried out in the absence of moisture.
25. A process as claimed in claim 23 or claim 24 wherein the reaction is effected in the presence of a solvent.
26. A process as claimed in claim 25 wherein the solvent comprises tetrahydrofuran , dioxan, dimethylformami-de or ethylene glycol dimethyl ether.
27. A process as claimed in claim 23 or 24 wherein the reaction is effected in the presence of an excess of the compound of formula Ilia used which excess acts as solvent.
28. A process as claimed in claim 23 or 24 wherein the reaction is effected in the absence of a solvent.
29. A process as claimed in any of claims 23 to 28 wherein the reaction is effected at temperatures of from 20 to 220°C.
30. A process as claimed in claim 29 wherein the reaction is effected at temperatures of from 60 to 200°C.
31. A process as claimed in any of claims 23 to 30 wherein a compound of formula II (wherein R represents a hydrogen atom) is reacted with a compound of formula Ilia (wherein one of the radicals X represents a group of formula OR^ wherein R∑. represents a lower alkyl group) and heating is continued for 10 to 70 hours whereby a compound of formula I wherein R,. represents a lower alkyl group is produced.
32. A process for the preparation of compounds of general formula I as defined in claim 1 which comprises reacting a compound of formula (wherein R.-, , R^ and R^ are as defined in claim 1 and the radicals R^, which may be the same or different, each represents a hydrogen atom, an optionally substituted alkyl, alkenyl or aryl group or the radicals R^ together with the nitrogen atom to which they are attached represent an optionally substituted heterocyclic ring) with an amine of formula H N (wherein and are as defined in claim 1 .
33. A process for the preparation of compounds general formula I as defined in claim 2 which comp reacting a (wherein , R^ and R,. are as defined in claim 1 and the radicals R^ , which may be the same or different, each represents a hydrogen atom, an optionally substituted alkyl, alkenyl or aryl group or the radicals ^ together with the nitrogen atom to which they are attached represent an optionally substituted heterocyclic ring) with an amine of formula (V) (wherein and are as defined in claim 2). 3 . A process as claimed in claim 32 or claim 33 wherein compound of formula IV (wherein the radicals represents alkyl groups containing from 1 to 3 carbon atoms) is used.
35. A process as claimed in any of claims 32 to 34 wherein the reaction is effected in the absence of moisture.
36. A process as claimed in any of claims 32 to 35 wherein the reaction is effected in the presence of an inert solvent.
37. A process as claimed in claim 36 wherein the solvent comprises tetrahydrofuran, dioxan or dimethyl-formamide.
38. A process as claimed in any of claims 32 to 35 wherein the reaction is effected in an excess of the amine of formula V used which excess serves as solvent.
39. A process as claimed in any of claims 32 to 38 wherein the reaction is effected in the presence of a catalytic quantity of a salt of the amine of formula V.
40. A process as claimed in claim 39 wherein the salt of the amino of formula V is the hydrochloride
41. A process as claimed in any of claims 32 to 40 wherein the reaction is effected at temperatures of from 50 to 160°C.
42. A process as claimed in claim 41 wherein the reaction is effected at temperatures of from 80 to 140°C.
43. A process as claimed in any of claims 32 to 42 wherein the reaction is effected in the absence of a solvent .
44. A process for the preparation of compounds of general formula I (wherein R^ to R,- are as defined in claim 1 with the proviso that R^ and R2 do not represent alkenyl or hydroxyalkyl groups and ^ and R^ , together with the nitrogen atom to which they are attached, do not represent a thiomorpholine-S-oxid o group) which comprise (wherein to are as defined in claim 1 with the proviso that and R do not represent alkenyl or hydroxyalkyl groups, and R^ and H^* together with the nitrogen atom to which they are attached, do not represent a thiomorpholine-S-oxide group).
45. A process as claimed in claim 44 wherein the rea-tion is effected in the presence of a solvent.
46. A process as claimed in claim 45 wherein the solvent comprises 4-methyl-cumene or quinoline.
47. A process as claimed in any of claims 44 to 46 wherein the dehydrogenation is effected using as dehydrogenating agent a noble metal , an oxide or . sulphide, sulphur or selenium.
48. A process as claimed in claim 47 wherein the noble metal is platinium, palladium or osmium.
49. A process as claimed in claim 47 wherein the oxide or sulphide is chromium (III) oxide or molybdenum disulphide.
50. A process as claimed in any of claims 44 to 49 wherein the dehydrogenation is effected at temperatures of from 100 to 250°C.
51. A process for the preparation of compound of general formula I as defined in claim 1 which comprises reacting a compound of formula or an alkali metal salt thereof or a compound of formula (wherein R^, R^ and R,. are as defined in claim 1, R^ is as defined for R,. with the proviso that it does not represent a hydrogen atom, and R-. represents an alkyl group with 1 to 5 carbon atoms) with an amine of formula (wherein and R are as defined in claim 1) or with an acid addition salt thereof.
52. A process as claimed in claim 51 wherein the reaction is carried out in the presence of an inert solvent chosen according to the starting materials.
53. A process as claimed in claim 52 wherein the solvent comprises benzene, ethanol, toluene, chloroform, methylene chloride, ether, tetrahydrofuran , dioxan or dimethyIforniamide.
54. A process as claimed in claim 51 wherein the reaction is effected in the presence of an excess of the amine of formula V used and/or an acid addition salt thereof which excess serves as solvent.
55. A process as claimed in claim 54 wherein the reaction is effected in the presence of an excess of the acetate or the hydrochloride of the amine of formula V used.
56. A process as claimed in claim 51 wherein the reaction is effected in the absence of a solvent.
57. A process as claimed in any of claims 51 to 55 wherein the reaction is effected at temperatures of from - v~ 0 to 250°C.
58. A process as claimed in any of claims 14 to 57 for the preparation of a compound of formula I wherein R, to R, are as defined in claim 1 and Rc is as defined 1 5 in claim 1 with the exception of the hydrogen atom which comprises the additional step of reacting the compound of formula I wherein R,- represents a hydrogen atom prepared according to any of claims 14 to 57 with a compound of formula X (VIII) (wherein R'^ is as defined in claim 1 for R,. with the exception of the hydrogen atom and X represents a chlorine, bromine or iodine atom or a p-toluenesulphonyl group).
59. A process as claimed in any of claims 14 to 20 and 33 for the preparation of a compound of formula I wherein R. to R. are as defined in claim 2 and Rc 1 4 5 is as defined in claim 2 with the exception of the hydrogen atom which comprises the additional step of reacting the compound of formula I wherein R^ represents a hydrogen atom prepared according to any of claims 14 to 20 and 33 with a compound of formula X R'J VIII (wherein is as defined in claim 2 for with the exception of the hydrogen atom and X represents a chlorine, bromine or iodine atom or a p-toluenesulphonyl group) . 60 A process as claimed in any of claims 23 to 31 and 44 to 57 for the preparation of a compound of formula I wherein R, to R, are as defined in claim 1 and 1 4 R^ is as defined in claim 1 with the exception of the hydrogen atom which comprises the additional step of reacting the compound of formula I wherein R^ represents a hydrogen atom prepared according to any of claims 23 to 31 and 44 to 57 with a compound of formula X R^ VIII (wherein R'^ is as defined in claim 1 for R,- with the exception of the hydrogen atom and X represents a chlorine, bromine or iodine atom or a p-toluenesulphonyl group). A process as claimed in any of claims 58 to 60 wherein the reaction is effected in the presence of a strong base.
62. A process as claimed in claim 61 wherein the strong base comprises sodium hydride or sodium methoxide.
63. A process as claimed in any of claims 58 to 62 wherein the reaction is effected in the presence of a solvent.
64. A process as claimed in claim 63 wherein the solvent comprises dimethylformamide.
65. A process as claimed in any of claims 58 to 64 wherein the reaction is effected at room temperature.
66. A process for the preparation of compounds of general formula I ( wherein R^ to R^ are as defined in claim 1 and R,. represents a lower alkyl group) which comprises reacting a compound of formula I (wherein R^ to R^ are as defined in claim 1 and R^ represents a hydrogen atom) obtained by any one of the processes claimed in claims 14 to 57 with a formamide diacetal of foimula III (wherein Rj. represents a lower alkyl group) at elevated temperatures.
67. A process for the preparation of compounds of general formula I (wherein R^ to R^ are as defined in claim 1 and R^. represents a lower alkyl group) which comprises reacting a compound of formula I (wherein R^ to R. are as defined in claim 1 and - represents a hydrogen atom) obtained by any one of the process claimed in claims 14 to 20 and 33 with a formamide diacetal of formula III (wherein Rj. represents a lower alkyl group) at elevated temperatures.
68. A process for the preparation of compounds of general formula I (wherein R^ to R^ are as defined in claim 1 and R<- represents a lower alkyl group) which comprises reacting a compound of formula I (wherein R^ to R^ are as defined in claim 1 and R,. represents a hydrogen atom) obtained by any one of the processes claimed in claims 23 to 31 and 44 to 57 with a formamide diacetal of formula III (wherein Rj. represents a lower alkyl group) at elevated temperatures.
69. A process for the preparation of compounds of general formula I as defined in claim 1 substantially as herein described.
70. A process for the preparation of compounds of general formula I as defined in claim 2 substantially as herein described. 7l!. A process for the preparation of compounds of general formula I as defined in claim 4 substantially as herein described.
72. A process for the preparation of compounds of general formula I as defined in claim 1 substantially as herein described with reference to Examples 1 to 200.
73. A process for the preparation of compounds of general formula I as defined in claim 2 substantially as herein described with reference to Examples 1 to 140.
74. A process for the preparation of compounds of general formula I as defined in claim 4 substantially as herein described with reference to Examples 141 to 168.
75. A process for the preparation of compounds of general formula I as defined in claim 1 substantially as herein described with reference to Examples 172 to 200.
76. Compounds of formula I as defined in claim 1 and acid addition salts thereof whenever prepared by a process as claimed in claims 14 to 75 .
77. Compounds of formula I as defined in claim 2 and acid addition salts thereof whenever prepared by a process as claimed in claims 14 to 20, 33,59,67, 70 and 73.
78. Compounds of formula I as defined in claim 4 and acid addition salts thereof whenever prepared by a process as claimed in claims 71 and 74.
79. Compounds of formula I as defined in claim 1 and acid addition salts thereof whenever prepared by a process as claimed in claims 23 to 31,44,to 57,60,68, and 75.
80. Pharmaceutical compositions comprising a compound of formula I, as defined in claim 1, or a physiologically acceptable acid addition salt thereof in association with a pharmaceutical carrier or excipient.
81. Pharmaceutical compositions comprising a compound of formula I, as defined in claim 2, or a physiologically acceptable acid addition salt thereof in association with a pharmaceutical carrier or excipient.
82. Pharmaceutical compositions comprising a compound . of formula I, as defined in claim 4, or a physiologically acceptable acid addition salt thereof in association with a pharmaceutical carrier or excipient.
83. Compositions as claimed in claims 80 to 82 in a form suitable for oral, rectal or parenteral administration.
84. Compositions as claimed in claims 80 to 83 in the form of tablets, coated tablets, capsules or suppositories. 42720/2
85. Compositions as claimed in any of claims 80 to 84 in the form of dosage units.
86. Compositions as claimed in claim 85 wherein each dosage unit contains from 2 to 20 mg of active ingredient 87· Compositions as claimed in claim 85 wherein each dosage unit contains from 5 to 10 mg of active ingredient.
88. Pharmaceutical compositions according to claim 80 substantially as herein described.
89. Pharmaceutical compositions according to claim 80 substantially as herein described with reference to Examples 201 to 207.
90. Pharmaceutical compositions according to claim 81 substantially as herein described, with reference to Examples 201 to 207.
IL42720A 1972-07-12 1973-07-11 5-phenyl-1,3-dihydro-3-aminomethylene-2h-1,4-benzodiazepin 2-one derivatives,their preparation and pharmaceutical compositions containing them IL42720A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19722234150 DE2234150A1 (en) 1972-07-12 1972-07-12 Benzodiazepin-2-one derivs - tranquillizers, sedatives, muscle relaxants
DE2324962A DE2324962A1 (en) 1973-05-15 1973-05-15 Benzodiazepin-2-one derivs - tranquillizers, sedatives, muscle relaxants
DE19732326657 DE2326657A1 (en) 1973-05-25 1973-05-25 Pharmacologically active 1,4-benzodiazepines - with sedative, tranquillising, muscle-relaxant and anti-convulsive activity

Publications (2)

Publication Number Publication Date
IL42720A0 IL42720A0 (en) 1973-11-28
IL42720A true IL42720A (en) 1976-06-30

Family

ID=27184564

Family Applications (1)

Application Number Title Priority Date Filing Date
IL42720A IL42720A (en) 1972-07-12 1973-07-11 5-phenyl-1,3-dihydro-3-aminomethylene-2h-1,4-benzodiazepin 2-one derivatives,their preparation and pharmaceutical compositions containing them

Country Status (15)

Country Link
JP (1) JPS4985080A (en)
AT (2) AT327922B (en)
AU (1) AU475257B2 (en)
BG (2) BG20802A3 (en)
CA (1) CA1006512A (en)
CH (1) CH590252A5 (en)
CS (1) CS176244B2 (en)
DD (1) DD106172A5 (en)
DK (1) DK138115C (en)
ES (1) ES416780A1 (en)
GB (1) GB1392143A (en)
HU (1) HU167867B (en)
IE (1) IE37904B1 (en)
IL (1) IL42720A (en)
PL (1) PL93110B1 (en)

Also Published As

Publication number Publication date
PL93110B1 (en) 1977-05-30
DK138115C (en) 1978-12-18
CS176244B2 (en) 1977-06-30
CA1006512A (en) 1977-03-08
AU5799773A (en) 1975-01-16
JPS4985080A (en) 1974-08-15
AT329572B (en) 1976-05-25
HU167867B (en) 1975-12-25
IE37904L (en) 1974-01-12
BG20374A3 (en) 1975-11-05
ES416780A1 (en) 1976-03-16
AU475257B2 (en) 1976-08-19
DD106172A5 (en) 1974-06-05
GB1392143A (en) 1975-04-30
AT327922B (en) 1976-02-25
ATA1008574A (en) 1975-08-15
DK138115B (en) 1978-07-17
BG20802A3 (en) 1975-12-20
CH590252A5 (en) 1977-07-29
IL42720A0 (en) 1973-11-28
ATA608873A (en) 1975-05-15
IE37904B1 (en) 1977-11-09

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