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1. (WO1998052930) NOVEL CYCLOBUTANE DERIVATIVES AND PROCESS FOR PRODUCING THE SAME
Latest bibliographic data on file with the International Bureau

Pub. No.: WO/1998/052930 International Application No.: PCT/JP1998/002206
Publication Date: 26.11.1998 International Filing Date: 20.05.1998
Chapter 2 Demand Filed: 08.10.1998
IPC:
C07C 43/315 (2006.01) ,C07C 62/08 (2006.01) ,C07C 67/347 (2006.01) ,C07C 69/757 (2006.01) ,C07D 263/38 (2006.01)
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
C
ACYCLIC OR CARBOCYCLIC COMPOUNDS
43
Ethers; Compounds having groups, groups or groups
30
Compounds having groups
315
containing oxygen atoms singly bound to carbon atoms not being acetal carbon atoms
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
C
ACYCLIC OR CARBOCYCLIC COMPOUNDS
62
Compounds having carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings and containing any of the groups OH, O-metal, -CHO, keto, ether, groups, groups, or groups
08
Saturated compounds containing ether groups, groups, groups, or groups
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
C
ACYCLIC OR CARBOCYCLIC COMPOUNDS
67
Preparation of carboxylic acid esters
30
by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
333
by isomerisation; by change of size of the carbon skeleton
343
by increase in the number of carbon atoms
347
by addition to unsaturated carbon-to-carbon bonds
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
C
ACYCLIC OR CARBOCYCLIC COMPOUNDS
69
Esters of carboxylic acids; Esters of carbonic or haloformic acids
74
Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring
757
having any of the groups OH, O-metal, -CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
C CHEMISTRY; METALLURGY
07
ORGANIC CHEMISTRY
D
HETEROCYCLIC COMPOUNDS
263
Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
02
not condensed with other rings
30
having two or three double bonds between ring members or between ring members and non-ring members
34
with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
36
One oxygen atom
38
attached in position 2
Applicants:
NIPPON KAYAKU KABUSHIKI KAISHA [JP/JP]; 11-2, Fujimi 1-chome Chiyoda-ku Tokyo 102-8172, JP (AllExceptUS)
NIITSUMA, Setsuko [JP/JP]; JP (UsOnly)
TSUDA, Makoto [JP/JP]; JP (UsOnly)
SATO, Hiroshi [JP/JP]; JP (UsOnly)
Inventors:
NIITSUMA, Setsuko; JP
TSUDA, Makoto; JP
SATO, Hiroshi; JP
Agent:
SAEKI, Norio; Taka-ai Building, 9th floor 15-2, Nihonbashi 3-chome, Chuo-ku Tokyo 103-0027, JP
Priority Data:
10/10476315.04.1998JP
10/11290009.04.1998JP
9/14450220.05.1997JP
9/15615730.05.1997JP
Title (EN) NOVEL CYCLOBUTANE DERIVATIVES AND PROCESS FOR PRODUCING THE SAME
(FR) NOUVEAUX DERIVES DE CYCLOBUTANE ET LEUR PROCEDE DE PRODUCTION
Abstract:
(EN) A process for producing cyclobutane derivatives useful as intermediates for cyclobutanenucleoside derivatives and the like useful as an antiviral agent; the novel intermediates; and a method for optical resolution. The cyclobutane derivatives can be efficiently produced under practical conditions. Optically active intermediates can be easily obtained. (a) The process is charecterized by using a magnesium-base Lewis acid as a catalyst in the production of a cyclobutane derivative through a [2+2] cycloaddition reaction shown by reaction scheme (I) (e.g., the condensation of a fumaric ester with a ketene derivative) wherein R5 and R6 each represents optionally substituted C1-20 linear, branched, or alicyclic alkyloxy (the substituents including (un)substituted phenyl) or a group represented by formula (4) (wherein A represents C2-5 alkylene; Y represents oxygen or sulfur; Z represents oxygen, sulfur, or -NR0-; and R0 represents hydrogen or a substituent); B1 and B2 each represents oxygen or sulfur; R4 represents hydrogen, C1-5 alkyl or alkoxy, or aralkyloxy; R7 and R8 each represents C1-5 alkyl, C7-10 aralkyl, or silyl, or represents C2-10 alkylene when R7 and R8 are bonded to each other to form a ring; R5 and R6, B1 and B2, and R7 and R8 each may be the same or different; and each double bond may be cis or trans. (b) In the optical resolution method, cyclobutanedicarboxylic acid derivatives derived from the cyclobutane derivatives or the like are optically resolved as salts thereof with an optionally substituted optically active N-benzyl-1-phenylethylamine.
(FR) L'invention concerne un procédé de production de dérivés de cyclobutane utiles en tant qu'intermédiaires de dérivés de cyclobutanenucléoside et analogue utiles en tant qu'agent antiviral, les nouveaux intermédiaires et un procédé de résolution optique. Les dérivés de cyclobutane peuvent être produits de manière efficace dans des conditions pratiques. Les intermédiaires actifs optiquement peuvent être obtenus facilement. Le procédé est caractérisé par l'utilisation d'un acide de Lewis à base de magnésium en tant que catalyseur dans la production d'un dérivé de cyclobutane par une réaction de cyclo-addition [2+2] illustrée par la réaction (I) (par exemple, la condensation d'un ester fumarique avec un dérivé de cétène), formule dans laquelle R5 et R6 représentent chacun alkyloxy C1-20 linéaire, ramifié ou alicyclique facultativement substitué (les substituants comprenant phényle substitué ou non substitué) ou un groupe représenté par la formule générale (4) (dans laquelle A représente alkylène C2-5; Y représente oxygène ou soufre; Z représente oxygène, soufre ou -NR0-; et R0 représente hydrogène ou un substituant); B1 et B2 représentent chacun oxygène ou soufre; R4 représente hydrogène, alkyle C1-5 ou alcoxy ou aralkyloxy; R7 et R8 représentent chacun alkyle C1-5, aralkyle C7-10 ou silyle, ou il représente alkylène C2-10 lorsque R7 et R8 sont liés l'un à l'autre pour former un cycle; R5 et R6, B1 et B2, ainsi que R7 et R8 peuvent chacun être identiques ou différents; et chaque double liaison peut être cis ou trans. Dans le procédé de résolution optique, les dérivés d'acide cyclobutane dicarboxylique dérivés des dérivés de cyclobutane ou analogue sont résolus optiquement sous forme de leurs sels avec une N-benzyl-1-phényléthylamine active optiquement et substituée facultativement.
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Designated States: CA, CN, JP, KR, US
European Patent Office (AT, BE, CH, CY, DE, DK, ES, FI, FR, GB, GR, IE, IT, LU, MC, NL, PT, SE)
Publication Language: Japanese (JA)
Filing Language: Japanese (JA)