FI73427C - FOERFARANDE FOER FRAMSTAELLNING AV 3-SUBSTITUERADE -KARBOLINER ANVAENDBARA SOM PSYKOFARMAKA. - Google Patents

Description

73427

Method for the preparation of 3-substituted β-carbolines useful as psychopharmaceuticals - For the preparation of 3-substituted β-carbolines useful as psychopharmaceuticals

The invention relates to a process for the preparation of 3-substituted β-carbolines of the general formula useful as psychopharmaceuticals.

H H

wherein R is H or an alkyl group having 1 to 6 carbon atoms,

Ra is H; Cl; br; J; CN; NO2; SCH 3; NR 1 R 4 wherein R 1 and R 2 are the same or different and each is H or an alkyl, alkenyl or alkynyl group having up to 3 carbon atoms or wherein R 1 and R 2 together with the nitrogen atom form a piperidine or methylpiperidine ring; group 0 I / OC2H5

- P

XOC2H5; a group -ch2-or6 wherein R® is H or C1-3 alkyl; -OR7, wherein R7 represents a C1-3 alkyl or benzyl group; a group -C = C - CH2 - O or a group -SO2Nr11r12- wherein R1 and R1 * are each C1-3 alkyl; 2 73427 rc is H, methyl, ethyl or a group -ch2-o-ch3> These new compounds have valuable pharmacological properties. They particularly affect the central nervous system and are suitable for use in psychopharmaceuticals.

Canadian Patent No. 786,351 discloses β-carboline-3-carboxylic acid amide derivatives substituted in the 1-position with an alkyl group containing no more than 5 carbon atoms, a trifluoromethyl, phenyl or benzyl group, and two compounds having no 1 in position. no substituent, namely β-carboline-3-carbohydrazine and β-carboline-3-carboxylic acid amide.

The specification of Danish Patent No. 98,436 describes a process for the preparation of 6-carboline-3-carboxylic acid methyl ester.

European Patent No. 30254 discloses β-carboline-3-carboxylic acid derivatives in the form of esters, amides and amidines and their thio analogues.

Danish Patents Nos. 100,952, 101,006 and 102,190 and GB Patent 975,835 describe β-carboline-3-carboxylic acid imides.

French Patent 1836 M and U.S. Patent 3,202,667 again describe 1-methyl-β-carbolines.

Finnish Patent No. 68829 discloses corresponding compounds having a carbonyl function in the 3-position.

The compounds of this invention differ from the prior art compounds in structure and, as shown in Table I below, are also significantly more active than the prior art compounds.

Compounds of formula I may be prepared by 1) a reactive derivative of a compound of formula II, preferably imidazolide,

RC

ΘΙ - COOH

B I] c I (II) 'Λγ · Ν

H H

wherein RA and have the same meaning as above are reacted with the formula

Ncm

R-C

With a compound of formula NH2, wherein R is as defined above, or

2) formula III

* -0cn $ r "* ·»

H H

wherein R and rC are as defined above is reacted with a compound of formula 4 73427 R-C (OCH3) 2N (CH3) 2 wherein R is as defined above to form a compound of general formula IV

RC

A [^ 11-jf / ^] - COIJ = CRN (CH3) 2

R CA '1 B 1 C N

CV) I 1

H H

wherein RA, R 1 and R 2 are as defined above, and the compound thus obtained is reacted with ΝΗ 2 tai or an amino compound such as O- (mesitylenesulfonyl) hydroxylamine, and if desired 3) the compound of formula I obtained, wherein RA is H is reacted with a halogenating agent or a nitrating agent to produce a compound of formula I wherein RA is Cl, Br or J, respectively NO2, or 4) a compound of formula I wherein RA is Cl, Br or J is reacted with diethyl phosphite to prepare a compound of formula I wherein RA is O

| / ° C2h5 - P

XOC2H5 or 5) a compound of formula I obtained in which RA is NO2 * is reduced to a compound of formula I in which RA is -ΝΗ2 ·

In preparing the compounds according to the above methods, further work-up can be carried out according to generally known methods, e.g., extraction, crystallization, chromatography, etc.

5 7ύ427

The starting materials used in Methods 1) and 2) can be prepared by methods known in the literature, e.g., from the specification of Canadian Patent No. 786,351.

To change the amino group in the A ring, a compound of formula (I) wherein R 1 is as defined above and R a is NH 2 may be reacted with an alkyl halide of formula R 1, R 2 Hal, wherein Hal is chlorine, bromine or iodine. and wherein R 1 and R 2 are as defined above, to form a compound of formula (I) wherein R and R c are as defined above and RA is NR 1 R 2.

The pharmacologically active compounds of the present invention can be used in the preparation of pharmaceutical preparations, e.g., for oral and parenteral administration to mammals, including humans, according to conventional methods of galenic pharmacy.

In general, the compounds of this invention are used in unit dosage forms of 0.05 to 10 mg in a pharmaceutically acceptable carrier per unit dose.

Doses of the compounds of this invention are 0.1 to 300 mg / day, preferably 1 to 30 mg / day, when administered as a medicament to patients, e.g., humans.

It is known [Squires, R.F., and Braestrup, C., Nature (London) 266 (1977) 734] that certain sites of the central nervous system of vertebrates have a particularly high affinity for the binding of 1,4- and 1,5-benzodiazepines. These sites are called benzodiazepine receptors.

The pharmacological properties of the compounds of this invention were studied by determining their ability to displace radiolabeled flunitrazepam from such benthaziazepine receptors.

6,7427 The displacement activity of the compounds of this invention has been determined based on the IC50 values and ED5Q values obtained.

IC 50 values represent the concentration at which 50% displacement (1.0 nM, 0 ° C) of specific binding of 3 H-furitrazepam occurs in samples with a total volume of 0.55 ml, e.g. in a rat membrane suspension.

Displacement experiments are performed as follows: 0.50 ml of untreated rat brain brain suspension in 25 mM KH 2 PO 4, pH 7.1 (5-10 mg tissue / sample) is incubated for 40-60 minutes at 0 ° C with 3 H-diazepam (specific activity 14.4 Ci / mmol, 1.9 nM) or with 3H-flunitrazepam (specific activity 87 Ci / mmol, 1.0 nM). After incubation, the suspension is filtered through a "Whatman GF / C" glass fiber filter, the filter cake is washed twice with cold buffer solution and the radioactivity is measured with a scintillation counter.

The experiment is repeated by adding a given amount or excess of the compound whose displacement property is to be determined before the addition of the radiolabeled benzodiazepine. Based on the measurement results obtained, IC50 values can be calculated.

The ED50 values represent the dose of test compound (mg / kg) at which the specific binding of flunitrazepam to benzodiazepine receptors in living brain tissue is reduced to 50% of control values. Such an in vivo test is performed as follows:

Groups of mice are injected with the test compound, using different doses and usually subcutaneously. 15 miles 73427 7 minutes later, β-flunitrazepam is administered intravenously to mice, and after 20 minutes, the mice are sacrificed and their forebrain membranes are separated and the radioactivity in the forebrain membranes is measured with a scintillation counter. EDjQ values are determined from dose-response curves.

The results obtained are shown in Table I, which also shows the compounds of the prior art for comparison.

8 73427

Table I Inhibition of 3 H-flunitrazepam binding

RC

H H

sp in vitro in vivo

Rrt IC50 ng / ml EDmg / kg

is

H H -c ^ I 0.56 15 - C - Me 6-Br H 2.8 26

is

H H -c ^ I 8.8 2 4 - c - <|

IS

H Et -c ^ J 4.5 31

- C - H O - N

6 ~ SO2NMe2 H -c ^ || 0.7 30 - c <]

IS

5- C1 H -c ^ I 5.2 18 N - C - Et 6 -OCH2Ph H 3.7 33 6- SMe H 1.1 23 6-CN H 1.1 19 6-NCX H <° 1, 6 · 9 56

N - C O

ra r1 X

DK 98436 H 1-Me C02Me 2040 DK 102190 H H CONH2 680> 100 In this divisional application No. 85 3073

M - O

H H 'CC I 7.5 15 - C - Et 9 73427

The invention will now be described in detail by the following examples. The examples illustrate specific embodiments of the invention and are to be construed as merely illustrative, but not restrictive, of the invention.

Example 1: N - [(dimethylamino) methylene] -3-carboline-3-carboxamide

A mixture of 1.0 g of β-carboline-3-carboxamide and 3 ml of dimethylformamide dimethyl acetal was heated for 3 hours in an oil bath at a temperature of about 115 ° C. After cooling, the crystals were collected on a glass filter and washed with 1 ml of dimethylformamide and then with 20 ml of ether. The yield was 1.2 g of N - [(dimethylamino) methylene] -β-carboline-3-carboxamide, m.p. 307-317 ° C.

% C% H% N

calculated 67.7 5.3 21.1 obtained 67.1 5.3 20.7

In a similar manner, N - [(dimethylamino) ethylidene] -N-carboline-3-carboxamide was prepared, m.p. 254-257 ° C.

Example 2: 3- (5- (3-methyl-1,2,4-oxadiazol) -yl) -β-carboline

A mixture of 1.3 ml of water, 1.3 ml of 4M sodium hydroxide, 7 ml of glacial acetic acid, 5 ml of dioxane, 0.35 g of hydroxylamine hydrochloride and 1.0 g of N - [(dimethylamino) ethylidene] -β-carboline -3-carboxamide, heated to 90 ° C (external temperature) for 2 hours. After cooling, 20 ml of water were added, after which the solid product was collected on a glass filter and washed with 40 ml of water. The yield was 0.8 g, m.p. 314-316 ° C, TLC: RF ^ 0.47.

_______ - TT

1 ° 73427

Example 3; 6-Bromo-3- (5- (3-methyl-1,2,4-oxadiazol) -yl) -β-carboline 2 ml of bromine in 20 ml of chloroform were added dropwise to a mixture of 1.0 g of 3 - (5- (3-methyl-1,2,4-oxadiazol) -yl) -β-carboline, 50 ml of chloroform and 3.5 ml of pyridine, at 0-5 ° C with stirring. After stirring for 2 hours at 0-5 ° C, 50 ml of chloroform was added, after which the solution was washed with sodium thiosulfate solution and then with water. The solution was dried over magnesium sulfate, filtered and evaporated to dryness to give 1.0 g of crude product. Recrystallization from pyridine gave 0.6 g of 6-bromo-3- (5- (3-methyl-1,2,4-oxadiazol) -yl) -β-carboline, m.p. 290-295 ° C. TLC: Rp = 1.05. Rpry.

Example 4; 3- (5- (3-methyl-1,2,4-oxadiazol) -yl) -6-nitro-β-carboline 1.0 g of 3- (5- (3-methyl-1,2,4) (oxadiazol) -yl) -β-carboline was added to 20 ml of concentrated nitric acid (65%). The mixture was stirred at room temperature for 2 hours. 100 g of ice water were added, after which the solid product was collected on a glass filter, washed with water and air-dried. Recrystallization from pyridine gave 0.6 g of 3- (5- (3-methyl-1,2,4-oxadiazol) -yl) -6-nitro-β-carboline, m.p. > 330 ° C, dec. TLC: Rf = 1.0 · Rp, Y-

Example 5: 6-Amino-3- (5- (3-methyl-1,2,4-oxadiazol) -yl) -β-carboline

A mixture of 0.2 g of 3- (5- (3-methyl-1,2,4-oxadiazo) yl) -6-nitro-β-carboline, 100 ml of 99% ethanol and 0.2 g of 5% palladium on carbon, hydrogenated at atmospheric pressure and u 73427 at room temperature. The mixture was then filtered and the solvent removed by evaporation to give 0.15 g of 6-amino-3- (5- (3-methyl-1,2,4-oxadiazol) -yl) -β-carboline, m.p. p. 310-320 ° C, dec. TLC: Rp = 0.61 · Rp, Y ·

Example 6: A. O-Carboline-3-carboxylic acid imidazolide 1.8 ml of thionyl chloride dissolved in 25 ml of dry tetrahydrofuran (THF) was added dropwise to 6.8 g of imidazole dissolved in 75 ml of dry THF. After stirring for 1 hour, the mixture was filtered and the filtrate was added dropwise to 2.65 g of dry β-carboline-3-carboxylic acid in 100 ml of dry dimethylformamide (DMF). The mixture was allowed to stand at 20 ° C until the next day.

In a similar manner there were prepared: 6-Bromo-β-carboline-3-carboxylic acid imidazolide 4-Ethyl-β-carboline-3-carboxylic acid imidazolide 6-Piperidine-β-carboline-3-carboxylic acid imidazolidine 6-Diallylamino-6-carboline-3-carboxylic acid Dipropargylamino-8-carboline-3-carboxylic acid imidazole 6-Dimethylsulfamoyl-β-carboline-3-carboxylic acid imidazole 4-Methoxymethyl-5-carboline-3-carboxylic acid imidazolidine 6-Chloro-β-carboline-3-carboline P-Carboline-3-carboxylic acid imidazolide 6-Nitro-P-carboline-3-carboxylic acid imidazolide 6- (4-methylpiperidino) -3-carboline-3-carboxylic acid imidazole 6-Benzyloxy-P-carboline-3-carboxylic acid imidazolidine 5- P-carboline-3-carboxylic acid imidazolide 6-Diallylamino-3-carboline-3-carboxylic acid imidazolide 6-methylthio-β-carboline-3-carboxylic acid imidazolide 12 73427 B. Propionamidoxime 2.3 g of sodium dissolved 40 any methanol, to 6.9 g of hydroxylamine hydrochloride dissolved in 100 any methanol was added. After standing for 1 hour, the mixture was filtered and 6.0 g of propionitrile was added to the filtrate. This mixture was allowed to stand for 2 days at room temperature.

Made in the same way! acetamidoxime starting from acetonitrile, bytyramidoxime starting from butyronitrile, valeramidoxime starting from valeronitrile, isobutyramidoxime starting from isobutyronitrile, vinylacetamidoxime starting from slycyclamide, allyl cyanide,

C. 3- (5 '- (3, -ethyl-1', 2 ', 4'-oxadiazol) -yl) -β-carboline

A solution of propionamidoxime in methanol was evaporated in vacuo with toluene. To the evaporated propionamidoxime was added a solution of β-carboline-3-carboxylic acid imidazolide in THF-DMF. The next day the mixture was evaporated in vacuo and 200 ml of toluene were added. This mixture was refluxed for 3 hours while stirring with a magnetic stirrer, then the warm mixture was filtered and the filtrate was evaporated. Addition of 20 mL H2O gave 1.5 g of crystalline product. Recrystallization from 15 ml of n-butanol gave 1.1 g of S-CS'-O'-ethyl-1 ', 2', 4'-oxadiazol) -yl) -3-carboline, m.p. 257- 260 ° C. TLCt Rp 0.50, CHCl3CH3CN t CH3OH t Et-jN = 18: 4: 2 tsp.

I! 13 73427

By the same procedure, but combining different carboxylic acid imidazolides with different amidoximes, the following compounds were prepared: 6-bromo-3- (5 '- (3'-methyl-1', 2 ', 4'-oxadiazol) -yl) - B-carboline, m.p. 353-358 ° C (dec.), 3- (5 '- (3'-ethyl-1', 2 ', 4'-oxadiazol) -yl) -β-carboline, m.p. 245-251 ° C, 4-ethyl-3- (5 '- (3'-methyl-1', 2 ', 4'-oxadiazol) -yl) -β-carboline, m.p. 266-268 ° C, 3- (51- (31-propyl-1 ', 2', 4 * -oxadiazol) -yl) -β-carboline, m.p. 187-208 ° C, 3- (5 '- (3'-butyl-1', 2 ', 4'-oxadiazol) -yl) -β-carboline, m.p. 208-211 ° C, 3- (5 '- (3'-ethyl-1', 2 ', 4'-oxadiazol) -yl) -6-piperidino-β-carboline, m.p. 152-170 ° C , 3- (5 * - (31-isopropyl-1 ', 2', 4'-oxadiazol) -yl) -f'-carboline, m.p. 220-225 ° C, 6-diallylamino-3- (5 '- (3'-methyl-1', 2 ', 4'-oxadiazol) -yl) -β-carboline, (dec.), 6-dipropargylamino- 3- (5 '- (3'-ethyl-1', 2 ', 41-oxadiazol) -yl) -β-carboline, m.p. 217-220 ° C, 6-diallylamino-3- (5 '- (3'-ethyl-1', 2 ', 4'-oxadiazol) -yl) -β-carboline, m.p. 181-186 ° C, 3- (5 '- (3'-allyl-1', 2 ', 4'-oxadiazol) -yl) -6-carboline, m.p. 194-205 ° C, 4-ethyl-3- (5 '- (3'-ethyl-1', 2 ', 4'-oxadiazol) -yl) -β-carboline, m.p. 235-240 ° C, 5'S'-O'-methoxymethyl-1 ', 2', 4'-oxadiazol) -yl) -p-carboline, m.p. 220-229 ° C, 6-diallylamino-3- (5 '- (3'-ethyl-1', 2 ', 4'-oxadiazol) -yl) -β-carboline, m.p. 154-160 ° C, 3- (5 '- (3'-cyclopropyl-1', 2 ', 4'-oxadiazol) -yl) -1'-carboline, m.p. 241-243 ° C, S-1'-O'-allyl-1 ', 2', 4'-oxadiazol) -yl) -6-diallylamino-6-carboline, m.p. 168-193 ° C, m.p. . ----- 14 73427 3- (5 * - (3'-phenyl-11,2 ', 4'-oxadiazol) -yl) -β-carboline, m.p. 275-278 ° C, 6-dimethylsulfamoyl-3- (5 '- (3'-ethyl-1', 2 ', 4'-oxadiazol) -yl) -β-carboline, m.p. 266-270 ° C, 3- (5 '- (3' - cyclopropyl-1,2,4-oxadiazol) -yl) -6-diallylamino-β-carboline, m.p. 131-143 ° C, 3- (5 '- (3'-cyclopropyl-1,2,4-oxadiazol) -yl) -6-dimethylsulfamoyl-β-carboline, m.p. 275-277 ° C, 3- (5 '- (3' -ethyl-1,2,4-oxadiazol) -yl) -4-methoxymethyl-5-carboline, m.p. 171-176 ° C, 6-chloro-3- (5 '- (3'-ethyl-1', 2 ', 4'-oxadiazol) -yl) -β-carboline, m.p. 300-312 ° C, 5-chloro-3- (5 '- (3'-ethyl-1,2,4-oxadiazol) -yl) -β-carboline, m.p. 299-309 ° C, 3- (5 '- (3' -ethyl-1,2,4-oxadiazol) -yl) -6-nitro-β-carboline, m.p. 333-338 ° C, 5-benzyloxy-3- (5 '- (3'-ethyl-1', 2 ', 4'-oxadiazol) -yl) -β-carboline, m.p. 215-218 ° C, 6-benzyloxy-3- (5 '- (3'-ethyl-1,2,4-oxadiazol) -yl) -β-carboline, m.p. 237-239 ° C, 3- (5 '- (3' -ethyl-1,2,4-oxadiazol) -yl) -6- (4-methylpiperidino) -β-carboline, m.p. 195-198 ° C, 3- (5 '- (3'-ethyl-1,2,4-oxadiazol) -yl) -6-methylthio) -β-carboline, m.p. 193-198 ° C, 6- (3-tetrahydropyran-2-yloxy-1-propynyl) -3- (5 '- (3'-ethyl-1', 2 ', 4'-oxadiazol) -yl) -β-carboline, m.p. 211-214 ° C, 6-cyano-3- (51- (3 * -ethyl-11,21,4'-oxadiazol) -yl) -β-carboline, m.p. 263-266 ° C, 6-methoxy-3- (5 '- (3'-ethyl-1,2,4-oxadiazol) -yl) - [- carboline, m.p. 178-182 ° C, 5-methoxymethyl-3- (5 '- (3'-ethyl-1,2,4-oxadiazol) -yl) -β-carboline, m.p. 207-211 ° C.

15 73427

Example 7; e-diethoxyphosphoryl-β-1S-O'-ethyl-1 ', 2', 4'-oxadiazol) -yl) -O-carboline 1> 6 g of e-iodo-S-CS'-O'-ethyl 1 ', 2', 4'-Oxadiazol) -yl) -β-carboline was added, under dry conditions, to a mixture of 608 mg of palladium tetrakistriphenylphosphine and 60 ml of N-methyl-2-pyrrolidone and stirred at 90 ° C for 12 hours. in. The mixture was evaporated in an oil pump vacuum, after which the evaporation residue was chromatographed on 75 g of silica gel, eluting with methylene chloride / acetone = 1: 1. The combined fractions were chromatographed on 25 g of silica gel, eluting with methylene chloride / ethanol = 10: 2 to give 425 mg of 6-diethoxyphosphoryl-3- (5 '- (3'-ethyl-1', 2 ', 4'-oxadiazole) - yl) -B-carboline, as an oil.

In a similar manner there were prepared: 6-diethoxyphosphoryl-4-methyl-3- (5, - (3, -ethyl-1 ', 2', 4'-oxadiazol) -yl) -6-carboline, as an oil, 6-diethoxyphosphoryl -4-methoxymethyl-3- (5 '- (3'-ethyl-1', 2 ', 4'-oxadiazol) -yl) -p-carboline as an oil.

Claims (1)

TT 16 73427 Claim: A process for the preparation of 3-substituted -carbolines of the general formula RC O - N a 1 n (I) rA - AB c * N - - RHH for use as psychopharmaceuticals in which R is H or 1 ~ An alkyl group having 6 carbon atoms, Ra is H; Cl; br; J; CN; N02; SCH 3; NRV, wherein R1 and R2 are the same or different and are each H or an alkyl, alkenyl or alkynyl group having up to 3 carbon atoms, or wherein R1 and together with the nitrogen atom form a piperidine or methylpiperidine ring; group 0! / OC2H5 - P NOC2H5; a group -ch2-or6 wherein R6 is H or C1-3 alkyl; -OR 1 f wherein R 2 represents a C 1-3 alkyl or benzyl group; a group -C = C - CH2 - O / O - or a group -SO2NR11R12, wherein R11 and R12 are each C3-3 alkyl; R * is H, methyl, ethyl or a group 73427 17 ~ CH2-O-CH3, characterized in that 1. a reactive derivative of a compound of formula II, preferably imidazolide, RC ι <ίΓ \ -— C00H (i,) HH wherein in formula RA and Rc are as defined above, is reacted with a compound of formula N ° H RC NH 2, wherein R is as defined above, or 2. a compound of formula III RC CONH, RA-f-AIB f Cl ON) HH, wherein RA and R 1 are as defined above are reacted with a compound of formula 73427 18 RC (OCH 3) 2 Nic 3) 2 wherein R is as defined above to form a compound of general formula IV RC »CON = CRN (CH 3) 2 ra I a II b He 'tlV) HH in which RA, Rc and R have the same meaning as above, and the compound thus obtained is reacted with ΝΗ2ΟΗ: η or an amino compound such as O- (mesitylenesulfonyl) -hydroxylamine, and, if desired, 3. a compound of formula I obtained wherein RA is H, is reacted with a halogenating agent or a nitrating agent to prepare a compound of formula I wherein RA is Cl, Br or J, respectively ΝO 2 »or 4. a compound of formula I wherein RA is Cl, Br or J is reacted with diethyl phosphite to prepare a compound of formula I wherein RA is O 1 / OC 2 H 5 - P 'NvOC 2 H 5 or 5. a compound of formula I wherein RA is NO 2 is reduced to a compound of formula I wherein RA is -NH 2 · I! 19 Patentkrav: 73427 Förfarande för framställning av soin psykofarmaka användbara 3-substituerade β-carboliner med den almänna forroeln pC J * O - N RA —B fTc ^ C <a, = NL- RHH i vilken R är H eller en alkylgrupp med 1 -6 cholatomer, Ra is H; Cl; br; J; CN; NO2; SCH 3; Nr1r2 ^ color R * and R2 are contaminated with oil or var och and is H, or alkyl, alkenyl or alkynyl with 3 coloraters or color R1 and R2 are optionally substituted with piperidine or methylpiperidine; Group 0 | ^ OC2H5 - P XvOC2H5; -CH2-OR6, color R6 and C1-3 alkyl; -OR7, color OR7 is C1-3 alkyl or benzyl; Group -c = c - ch2 - o ^ eller Gruppen-SO2NRHRl2, color R ^ och R ^ 2 var och en är en Cx_3 ~ - lagalkyl; C .. R ar H, methyl, ethyl or groups 20 -ch2-o-ch3, 73427 are shown in Figure 1 as a reactive derivative, especially imidazolide, in the form of a compound RC —COOH RA — PA |] ^ B Jlc I 00 HH i vilken RA och R <- betecknar decamma som ovan, omsätts med en förening med formuleln NOH Rc ^ NH2 i vilken R betecknar decamma som ovan, eller 2. en förening med formuleln III RC —CONH- HH i vilken RÄ and Rc deck number in the form of an RC, OCH3) (CH3) 2 »i vilken R deck number in the form of an RC, OCH3) (CH3) 2