CA2012096C - Composes de cytosine et procede de production - Google Patents

Composes de cytosine et procede de production

Info

Publication number: CA2012096C
Authority: CA; Canada
Prior art keywords: group; formula; compound; hydrogen; process defined
Prior art date: 1990-03-13
Legal status (The legal status 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 status listed.): Expired - Lifetime

Application number

CA 2012096

Other languages

English (en)

Other versions

CA2012096A1 (fr

Inventor

Khashayar Karimian

Bruno Konrad Radatus

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Apotex Pharmachem Inc

Original Assignee

Acic Canada Inc

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.)

1990-03-13

Filing date

1990-03-13

Publication date

1997-10-28

1990-03-13 Priority to CA 2012096 priority Critical patent/CA2012096C/fr

1990-03-13 Application filed by Acic Canada Inc filed Critical Acic Canada Inc

1991-03-13 Priority to PCT/CA1991/000078 priority patent/WO1991013901A1/fr

1991-03-13 Priority to US07/930,605 priority patent/US5399682A/en

1991-03-13 Priority to BR919106157A priority patent/BR9106157A/pt

1991-03-13 Priority to AT91906308T priority patent/ATE125265T1/de

1991-03-13 Priority to HU9202905A priority patent/HUT61565A/hu

1991-03-13 Priority to DE69111438T priority patent/DE69111438T2/de

1991-03-13 Priority to EP91906308A priority patent/EP0523080B1/fr

1991-03-13 Priority to AU74801/91A priority patent/AU7480191A/en

1991-09-13 Publication of CA2012096A1 publication Critical patent/CA2012096A1/fr

1994-02-02 Priority to US08/191,192 priority patent/US5527782A/en

1994-12-15 Priority to US08/356,498 priority patent/US5536824A/en

1995-06-06 Priority to US08/469,506 priority patent/US5596093A/en

1997-10-28 Application granted granted Critical

1997-10-28 Publication of CA2012096C publication Critical patent/CA2012096C/fr

2010-03-13 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 27
238000004519 manufacturing process Methods 0.000 title abstract description 16
OPTASPLRGRRNAP-UHFFFAOYSA-N cytosine Chemical class NC=1C=CNC(=O)N=1 OPTASPLRGRRNAP-UHFFFAOYSA-N 0.000 title description 18
150000001875 compounds Chemical class 0.000 claims abstract description 40
-1 methoxytrityl Chemical group 0.000 claims abstract description 26
150000003839 salts Chemical class 0.000 claims abstract description 17
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 16
239000001257 hydrogen Substances 0.000 claims abstract description 16
125000003118 aryl group Chemical group 0.000 claims abstract description 9
125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims abstract description 9
125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 claims abstract description 8
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims abstract description 8
229910019142 PO4 Inorganic materials 0.000 claims abstract description 8
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims abstract description 8
125000005251 aryl acyl group Chemical group 0.000 claims abstract description 8
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims abstract description 8
235000021317 phosphate Nutrition 0.000 claims abstract description 8
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims abstract description 8
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 7
125000005257 alkyl acyl group Chemical group 0.000 claims abstract description 7
150000003013 phosphoric acid derivatives Chemical class 0.000 claims abstract description 7
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 6
125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 11
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 10
150000002431 hydrogen Chemical class 0.000 claims description 10
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 10
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 9
229910000041 hydrogen chloride Inorganic materials 0.000 claims description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
230000008707 rearrangement Effects 0.000 claims description 7
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
239000000203 mixture Substances 0.000 claims description 5
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
239000002798 polar solvent Substances 0.000 claims description 4
238000010992 reflux Methods 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
229910052736 halogen Inorganic materials 0.000 claims description 3
150000002367 halogens Chemical class 0.000 claims description 3
229910000039 hydrogen halide Inorganic materials 0.000 claims description 3
239000012433 hydrogen halide Substances 0.000 claims description 3
238000009835 boiling Methods 0.000 claims description 2
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 2
150000003841 chloride salts Chemical class 0.000 claims 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 1
239000010452 phosphate Substances 0.000 claims 1
230000007935 neutral effect Effects 0.000 abstract description 2
230000006820 DNA synthesis Effects 0.000 abstract 1
230000005764 inhibitory process Effects 0.000 abstract 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 35
238000006243 chemical reaction Methods 0.000 description 13
229950000242 ancitabine Drugs 0.000 description 10
150000001412 amines Chemical class 0.000 description 9
229940104302 cytosine Drugs 0.000 description 9
239000002904 solvent Substances 0.000 description 7
239000003125 aqueous solvent Substances 0.000 description 5
239000013078 crystal Substances 0.000 description 5
YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 5
230000008878 coupling Effects 0.000 description 4
238000010168 coupling process Methods 0.000 description 4
238000005859 coupling reaction Methods 0.000 description 4
239000000047 product Substances 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
239000007858 starting material Substances 0.000 description 4
239000006188 syrup Substances 0.000 description 4
235000020357 syrup Nutrition 0.000 description 4
UHDGCWIWMRVCDJ-UHFFFAOYSA-N 1-beta-D-Xylofuranosyl-NH-Cytosine Natural products O=C1N=C(N)C=CN1C1C(O)C(O)C(CO)O1 UHDGCWIWMRVCDJ-UHFFFAOYSA-N 0.000 description 3
UHDGCWIWMRVCDJ-PSQAKQOGSA-N Cytidine Natural products O=C1N=C(N)C=CN1[C@@H]1[C@@H](O)[C@@H](O)[C@H](CO)O1 UHDGCWIWMRVCDJ-PSQAKQOGSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
230000000903 blocking effect Effects 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 2
VLIXZEKAVFLJRY-UJDVCPFMSA-N 4-amino-1-[(2r,3s,4r,5r)-3,4-dihydroxy-5-(hydroxymethyl)-4-(4-methylphenyl)sulfonyloxolan-2-yl]pyrimidin-2-one Chemical compound C1=CC(C)=CC=C1S(=O)(=O)[C@]1(O)[C@@H](O)[C@H](N2C(N=C(N)C=C2)=O)O[C@@H]1CO VLIXZEKAVFLJRY-UJDVCPFMSA-N 0.000 description 2
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
239000002178 crystalline material Substances 0.000 description 2
UHDGCWIWMRVCDJ-ZAKLUEHWSA-N cytidine Chemical compound O=C1N=C(N)C=CN1[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O1 UHDGCWIWMRVCDJ-ZAKLUEHWSA-N 0.000 description 2
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
238000001228 spectrum Methods 0.000 description 2
238000003756 stirring Methods 0.000 description 2
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
WCXOOVODAUHPMZ-VDSQZSGCSA-N 4-amino-1-[(2R,3S,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)-4-(4-methylphenyl)sulfonyloxolan-2-yl]pyrimidin-2-one ethanol Chemical compound C(C)O.S(=O)(=O)(C1=CC=C(C)C=C1)[C@@]1([C@H]([C@@H](O[C@@H]1CO)N1C(=O)N=C(N)C=C1)O)O WCXOOVODAUHPMZ-VDSQZSGCSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
NIDVTARKFBZMOT-PEBGCTIMSA-N N(4)-acetylcytidine Chemical compound O=C1N=C(NC(=O)C)C=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 NIDVTARKFBZMOT-PEBGCTIMSA-N 0.000 description 1
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
239000012346 acetyl chloride Substances 0.000 description 1
238000013019 agitation Methods 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
KZOWNALBTMILAP-JBMRGDGGSA-N ancitabine hydrochloride Chemical class Cl.N=C1C=CN2[C@@H]3O[C@H](CO)[C@@H](O)[C@@H]3OC2=N1 KZOWNALBTMILAP-JBMRGDGGSA-N 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 description 1
SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
230000002950 deficient Effects 0.000 description 1
238000010511 deprotection reaction Methods 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000012458 free base Substances 0.000 description 1
230000013595 glycosylation Effects 0.000 description 1
238000006206 glycosylation reaction Methods 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
FIQMVMWAWILUDW-KYJNYJMBSA-N n-[1-[(2r,3r,4r,5r)-4-hydroxy-3-trityloxy-5-(trityloxymethyl)oxolan-2-yl]-2-oxopyrimidin-4-yl]acetamide Chemical compound O=C1N=C(NC(=O)C)C=CN1[C@H]1[C@H](OC(C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)[C@H](O)[C@@H](COC(C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)O1 FIQMVMWAWILUDW-KYJNYJMBSA-N 0.000 description 1
239000012264 purified product Substances 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000000243 solution Substances 0.000 description 1
230000002269 spontaneous effect Effects 0.000 description 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
238000005406 washing Methods 0.000 description 1
238000005303 weighing Methods 0.000 description 1

Landscapes

Saccharide Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA 2012096 1990-03-13 1990-03-13 Composes de cytosine et procede de production Expired - Lifetime CA2012096C (fr)

Priority Applications (12)

Application Number	Priority Date	Filing Date	Title
CA 2012096 CA2012096C (fr)	1990-03-13	1990-03-13	Composes de cytosine et procede de production
AU74801/91A AU7480191A (en)	1990-03-13	1991-03-13	3'-o-tosylcytidine and cytosine compounds, and process for production thereof
BR919106157A BR9106157A (pt)	1990-03-13	1991-03-13	Compostos e processo 3'-o-tosil citidina e citosina e processo para producao dos mesmos
AT91906308T ATE125265T1 (de)	1990-03-13	1991-03-13	2,3'-o-cyclocytidine und verfahren zu deren herstellung.
HU9202905A HUT61565A (en)	1990-03-13	1991-03-13	Process for producing 2,3'-0-cyclocytidine and 1-(beta-d-xylopento-furanosyl)-cytosine derivatives and their analogous compounds, as well as 3'-0-(p-toluenesulfonyl)-cytidine derivatives
DE69111438T DE69111438T2 (de)	1990-03-13	1991-03-13	2,3'-o-cyclocytidine und verfahren zu deren herstellung.
PCT/CA1991/000078 WO1991013901A1 (fr)	1990-03-13	1991-03-13	Composes de tosylcytidine-3'-0 et de cytosine, et leur procede de production
US07/930,605 US5399682A (en)	1990-03-13	1991-03-13	Process for preparing 2,3'-O-cyclocytidine
EP91906308A EP0523080B1 (fr)	1990-03-13	1991-03-13	Composes de 2,3'-o-cyclocytidine, et leur procede de production
US08/191,192 US5527782A (en)	1990-03-13	1994-02-02	5-halo-2,3'-O-cyclocytidines
US08/356,498 US5536824A (en)	1990-03-13	1994-12-15	Organosulfonyl salts of 2,3'-O-cyclocytidine
US08/469,506 US5596093A (en)	1990-03-13	1995-06-06	Process for preparing halogenated 2,3-O-cyclocytidine derivatives

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA 2012096 CA2012096C (fr)	1990-03-13	1990-03-13	Composes de cytosine et procede de production

Publications (2)

Publication Number	Publication Date
CA2012096A1 CA2012096A1 (fr)	1991-09-13
CA2012096C true CA2012096C (fr)	1997-10-28

Family

ID=4144518

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA 2012096 Expired - Lifetime CA2012096C (fr)	1990-03-13	1990-03-13	Composes de cytosine et procede de production

Country Status (1)

Country	Link
CA (1)	CA2012096C (fr)

1990
- 1990-03-13 CA CA 2012096 patent/CA2012096C/fr not_active Expired - Lifetime

Also Published As

Publication number	Publication date
CA2012096A1 (fr)	1991-09-13

Legal Events

Date	Code	Title	Description
1990-07-13	EEER	Examination request
2010-03-13	MKEX	Expiry

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