CA2302630A1 - Purine acyclonucleosides as antiviral agents - Google Patents

Purine acyclonucleosides as antiviral agents Download PDF

Info

Publication number: CA2302630A1
Authority: CA; Canada
Prior art keywords: hydroxy; amino; hydrogen; compound; formula
Prior art date: 1997-09-11
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.): Abandoned

Application number

CA002302630A

Other languages

English (en)

French (fr)

Inventor

Karen Elizabeth Jarvis

Sebastian Mario Marcuccio

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.)

Commonwealth Scientific and Industrial Research Organization CSIRO

Original Assignee

Individual

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.)

1997-09-11

Filing date

1998-09-11

Publication date

1999-03-18

1998-09-11 Application filed by Individual filed Critical Individual

1999-03-18 Publication of CA2302630A1 publication Critical patent/CA2302630A1/en

Status Abandoned legal-status Critical Current

Links

KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 title description 20
239000003443 antiviral agent Substances 0.000 title description 5
150000001875 compounds Chemical class 0.000 claims abstract description 90
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 37
-1 hydrazino, hydroxylamino, benzyloxy Chemical group 0.000 claims abstract description 32
150000003839 salts Chemical class 0.000 claims abstract description 31
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 28
239000001257 hydrogen Substances 0.000 claims abstract description 28
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 27
150000002431 hydrogen Chemical group 0.000 claims abstract description 24
238000011282 treatment Methods 0.000 claims abstract description 20
125000003545 alkoxy group Chemical group 0.000 claims abstract description 19
125000000217 alkyl group Chemical group 0.000 claims abstract description 17
125000003282 alkyl amino group Chemical group 0.000 claims abstract description 16
125000004414 alkyl thio group Chemical group 0.000 claims abstract description 16
125000004104 aryloxy group Chemical group 0.000 claims abstract description 16
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims abstract description 16
229910052736 halogen Inorganic materials 0.000 claims abstract description 16
150000002367 halogens Chemical group 0.000 claims abstract description 16
125000003118 aryl group Chemical group 0.000 claims abstract description 14
208000036142 Viral infection Diseases 0.000 claims abstract description 13
238000011321 prophylaxis Methods 0.000 claims abstract description 13
125000000446 sulfanediyl group Chemical group *S* 0.000 claims abstract description 13
230000009385 viral infection Effects 0.000 claims abstract description 13
208000002672 hepatitis B Diseases 0.000 claims abstract description 10
238000000034 method Methods 0.000 claims description 44
150000002148 esters Chemical class 0.000 claims description 15
238000001727 in vivo Methods 0.000 claims description 12
ANFNNSIOGODJDN-UHFFFAOYSA-N 2-amino-9-[3-hydroxy-2-(hydroxymethyl)propyl]-3h-purin-6-one Chemical compound N1C(N)=NC(=O)C2=C1N(CC(CO)CO)C=N2 ANFNNSIOGODJDN-UHFFFAOYSA-N 0.000 claims description 9
239000003085 diluting agent Substances 0.000 claims description 7
239000003814 drug Substances 0.000 claims description 7
238000004519 manufacturing process Methods 0.000 claims description 5
239000003937 drug carrier Substances 0.000 claims description 4
239000008194 pharmaceutical composition Substances 0.000 claims description 4
PIWJGZWZNOWIGH-UHFFFAOYSA-N 2-[(2-aminopurin-9-yl)methyl]propane-1,3-diol Chemical compound NC1=NC=C2N=CN(CC(CO)CO)C2=N1 PIWJGZWZNOWIGH-UHFFFAOYSA-N 0.000 claims description 3
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 3
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 3
125000004430 oxygen atom Chemical group O* 0.000 claims description 3
ULDVPVQNHPIANB-UHFFFAOYSA-N 2-[(6-aminopurin-9-yl)methyl]propane-1,3-diol Chemical compound NC1=NC=NC2=C1N=CN2CC(CO)CO ULDVPVQNHPIANB-UHFFFAOYSA-N 0.000 claims description 2
KNFZVBOYMBHOOV-UHFFFAOYSA-N 2-amino-9-[(2-propan-2-yl-1,3-dioxan-5-yl)methyl]-3h-purin-6-one Chemical compound C1OC(C(C)C)OCC1CN1C(NC(N)=NC2=O)=C2N=C1 KNFZVBOYMBHOOV-UHFFFAOYSA-N 0.000 claims description 2
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OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 66
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 60
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239000003795 chemical substances by application Substances 0.000 description 8
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IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 6
239000002253 acid Substances 0.000 description 6
229940024606 amino acid Drugs 0.000 description 6
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150000005690 diesters Chemical class 0.000 description 6
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229910052740 iodine Inorganic materials 0.000 description 6
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235000019341 magnesium sulphate Nutrition 0.000 description 6
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 6
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238000005406 washing Methods 0.000 description 6
NDQXKKFRNOPRDW-UHFFFAOYSA-N 1,1,1-triethoxyethane Chemical compound CCOC(C)(OCC)OCC NDQXKKFRNOPRDW-UHFFFAOYSA-N 0.000 description 5
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FZAUKSQGKWDVJI-UHFFFAOYSA-N [2-(acetyloxymethyl)-3-methylsulfonyloxypropyl] acetate Chemical compound CC(=O)OCC(COC(C)=O)COS(C)(=O)=O FZAUKSQGKWDVJI-UHFFFAOYSA-N 0.000 description 5
125000002015 acyclic group Chemical group 0.000 description 5
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239000012043 crude product Substances 0.000 description 5
125000000524 functional group Chemical group 0.000 description 5
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238000009505 enteric coating Methods 0.000 description 1
230000002255 enzymatic effect Effects 0.000 description 1
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
230000007717 exclusion Effects 0.000 description 1
238000000605 extraction Methods 0.000 description 1
229960004396 famciclovir Drugs 0.000 description 1
GGXKWVWZWMLJEH-UHFFFAOYSA-N famcyclovir Chemical compound N1=C(N)N=C2N(CCC(COC(=O)C)COC(C)=O)C=NC2=C1 GGXKWVWZWMLJEH-UHFFFAOYSA-N 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
235000013355 food flavoring agent Nutrition 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
229960002963 ganciclovir Drugs 0.000 description 1
210000001035 gastrointestinal tract Anatomy 0.000 description 1
239000000499 gel Substances 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
235000011187 glycerol Nutrition 0.000 description 1
125000004438 haloalkoxy group Chemical group 0.000 description 1
125000001188 haloalkyl group Chemical group 0.000 description 1
206010073071 hepatocellular carcinoma Diseases 0.000 description 1
231100000844 hepatocellular carcinoma Toxicity 0.000 description 1
125000005842 heteroatom Chemical group 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
235000012907 honey Nutrition 0.000 description 1
210000005260 human cell Anatomy 0.000 description 1
150000004677 hydrates Chemical class 0.000 description 1
125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 description 1
239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 1
239000012535 impurity Substances 0.000 description 1
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
HOBCFUWDNJPFHB-UHFFFAOYSA-N indolizine Chemical compound C1=CC=CN2C=CC=C21 HOBCFUWDNJPFHB-UHFFFAOYSA-N 0.000 description 1
239000003701 inert diluent Substances 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
230000000266 injurious effect Effects 0.000 description 1
229910052816 inorganic phosphate Inorganic materials 0.000 description 1
229940047122 interleukins Drugs 0.000 description 1
238000010255 intramuscular injection Methods 0.000 description 1
238000010253 intravenous injection Methods 0.000 description 1
229960000310 isoleucine Drugs 0.000 description 1
AGPKZVBTJJNPAG-UHFFFAOYSA-N isoleucine Natural products CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 description 1
QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 1
CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
239000010410 layer Substances 0.000 description 1
239000010501 lemon oil Substances 0.000 description 1
QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
208000019423 liver disease Diseases 0.000 description 1
CJPLEFFCVDQQFZ-UHFFFAOYSA-N loviride Chemical compound CC(=O)C1=CC=C(C)C=C1NC(C(N)=O)C1=C(Cl)C=CC=C1Cl CJPLEFFCVDQQFZ-UHFFFAOYSA-N 0.000 description 1
229950006243 loviride Drugs 0.000 description 1
239000007937 lozenge Substances 0.000 description 1
239000002207 metabolite Substances 0.000 description 1
229910000000 metal hydroxide Inorganic materials 0.000 description 1
150000004692 metal hydroxides Chemical class 0.000 description 1
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
125000002950 monocyclic group Chemical group 0.000 description 1
239000002324 mouth wash Substances 0.000 description 1
125000001419 myristoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
239000012457 nonaqueous media Substances 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
229940127073 nucleoside analogue Drugs 0.000 description 1
239000002773 nucleotide Substances 0.000 description 1
125000003729 nucleotide group Chemical group 0.000 description 1
239000002674 ointment Substances 0.000 description 1
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
238000003305 oral gavage Methods 0.000 description 1
239000010502 orange oil Substances 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
125000001312 palmitoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
235000010603 pastilles Nutrition 0.000 description 1
239000008188 pellet Substances 0.000 description 1
239000000137 peptide hydrolase inhibitor Substances 0.000 description 1
239000008177 pharmaceutical agent Substances 0.000 description 1
YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 1
GJSGGHOYGKMUPT-UHFFFAOYSA-N phenoxathiine Chemical compound C1=CC=C2OC3=CC=CC=C3SC2=C1 GJSGGHOYGKMUPT-UHFFFAOYSA-N 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 1
150000003014 phosphoric acid esters Chemical class 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical compound C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 description 1
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
229920000053 polysorbate 80 Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
229940069328 povidone Drugs 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
230000002335 preservative effect Effects 0.000 description 1
CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical compound N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 description 1
230000005180 public health Effects 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000012521 purified sample Substances 0.000 description 1
PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
150000003242 quaternary ammonium salts Chemical class 0.000 description 1
JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000011160 research Methods 0.000 description 1
230000004044 response Effects 0.000 description 1
238000002390 rotary evaporation Methods 0.000 description 1
238000011894 semi-preparative HPLC Methods 0.000 description 1
UQDJGEHQDNVPGU-UHFFFAOYSA-N serine phosphoethanolamine Chemical compound [NH3+]CCOP([O-])(=O)OCC([NH3+])C([O-])=O UQDJGEHQDNVPGU-UHFFFAOYSA-N 0.000 description 1
238000007493 shaping process Methods 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
229940080313 sodium starch Drugs 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
JJICLMJFIKGAAU-UHFFFAOYSA-M sodium;2-amino-9-(1,3-dihydroxypropan-2-yloxymethyl)purin-6-olate Chemical compound [Na+].NC1=NC([O-])=C2N=CN(COC(CO)CO)C2=N1 JJICLMJFIKGAAU-UHFFFAOYSA-M 0.000 description 1
RMLUKZWYIKEASN-UHFFFAOYSA-M sodium;2-amino-9-(2-hydroxyethoxymethyl)purin-6-olate Chemical compound [Na+].O=C1[N-]C(N)=NC2=C1N=CN2COCCO RMLUKZWYIKEASN-UHFFFAOYSA-M 0.000 description 1
239000012265 solid product Substances 0.000 description 1
239000012453 solvate Substances 0.000 description 1
238000007614 solvation Methods 0.000 description 1
239000008174 sterile solution Substances 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
238000010254 subcutaneous injection Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000000758 substrate Substances 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
GVIJJXMXTUZIOD-UHFFFAOYSA-N thianthrene Chemical compound C1=CC=C2SC3=CC=CC=C3SC2=C1 GVIJJXMXTUZIOD-UHFFFAOYSA-N 0.000 description 1
229960003087 tioguanine Drugs 0.000 description 1
238000011200 topical administration Methods 0.000 description 1
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
AGZPNUZBDCYTBB-UHFFFAOYSA-N triethyl methanetricarboxylate Chemical compound CCOC(=O)C(C(=O)OCC)C(=O)OCC AGZPNUZBDCYTBB-UHFFFAOYSA-N 0.000 description 1
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
238000000825 ultraviolet detection Methods 0.000 description 1
229960005486 vaccine Drugs 0.000 description 1
239000004474 valine Substances 0.000 description 1
239000003643 water by type Substances 0.000 description 1
239000008215 water for injection Substances 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/18—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 one oxygen and one nitrogen atom, e.g. guanine
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/20—Antivirals for DNA viruses
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/16—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two nitrogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/26—Heterocyclic compounds containing purine ring systems with an oxygen, sulphur, or nitrogen atom directly attached in position 2 or 6, but not in both
- C07D473/32—Nitrogen atom
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/26—Heterocyclic compounds containing purine ring systems with an oxygen, sulphur, or nitrogen atom directly attached in position 2 or 6, but not in both
- C07D473/36—Sulfur atom

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Virology (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Oncology (AREA)
Molecular Biology (AREA)
Chemical Kinetics & Catalysis (AREA)
Biotechnology (AREA)
Medicinal Chemistry (AREA)
Communicable Diseases (AREA)
Engineering & Computer Science (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA002302630A 1997-09-11 1998-09-11 Purine acyclonucleosides as antiviral agents Abandoned CA2302630A1 (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
AUPO9129A AUPO912997A0 (en)	1997-09-11	1997-09-11	Antiviral agents
AUPO9129		1997-09-11
PCT/AU1998/000748 WO1999012927A1 (en)	1997-09-11	1998-09-11	Purine acyclonucleosides as antiviral agents

Publications (1)

Publication Number	Publication Date
CA2302630A1 true CA2302630A1 (en)	1999-03-18

Family

ID=3803414

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002302630A Abandoned CA2302630A1 (en)	1997-09-11	1998-09-11	Purine acyclonucleosides as antiviral agents

Country Status (9)

Country	Link
EP (1)	EP1019404A4 (id)
JP (1)	JP2001515900A (id)
KR (1)	KR20010023890A (id)
CN (1)	CN1269801A (id)
AU (1)	AUPO912997A0 (id)
CA (1)	CA2302630A1 (id)
ID (1)	ID26937A (id)
NZ (1)	NZ502994A (id)
WO (1)	WO1999012927A1 (id)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
SI20022A (sl) *	1998-07-29	2000-02-29	Kemijski inštitut	Alkilno substituirani purinovi derivati in njihova priprava
KR100377138B1 (ko) *	1998-11-10	2003-06-12	주식회사 엘지생명과학	퓨린구조를갖는싸이클린의존키나아제저해제,그제조방법및그를함유하는항암제조성물
GB9903762D0 (en)	1999-02-18	1999-04-14	Novartis Ag	Organic compounds
CA2405151A1 (en) *	2000-04-07	2001-10-18	University Of Maryland, Baltimore	Bile acid containing prodrugs with enhanced bioavailability
US7241890B2 (en)	2001-10-30	2007-07-10	Conforma Therapeutics Corporation	Purine analogs having HSP90-inhibiting activity
DE60313173T2 (de) *	2002-06-27	2008-01-03	F. Hoffmann-La Roche Ag	Synthese von purin-derivaten
EP1615926A1 (en) *	2003-04-21	2006-01-18	Ustav Organicke Chemie A Biochemie Akademie Ved Ceske Republiky	(purin-6-yl) amino acid and production method thereof
KR20060070572A (ko)	2003-09-18	2006-06-23	콘포마 세러퓨틱스 코포레이션	Ｈｓｐ90-저해제로서의 신규 헤테로시클릭 화합물
CA2602257A1 (en)	2005-03-30	2006-10-05	Conforma Therapeutics Corporation	Alkynyl pyrrolopyrimidines and related analogs as hsp90-inhibitors
CN102002043B (zh) *	2010-11-16	2012-10-24	江苏科技大学	4-氨基吡啶催化下的6-甲氧基嘌呤衍生物的合成方法
CN102633767B (zh) *	2012-04-09	2013-10-30	武汉工程大学	一种非离子型碘造影剂中间体2－异丙基－5－羧基－1，3－二氧六环的制备方法
AU2017320742B2 (en) *	2016-08-29	2021-08-05	F. Hoffmann-La Roche Ag	7-substituted sulfonimidoylpurinone compounds for the treatment and prophylaxis of virus infection

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5216141A (en) *	1988-06-06	1993-06-01	Benner Steven A	Oligonucleotide analogs containing sulfur linkages
GB8904855D0 (en) *	1989-03-03	1989-04-12	Beecham Group Plc	Pharmaceutical treatment

1997
- 1997-09-11 AU AUPO9129A patent/AUPO912997A0/en not_active Abandoned
1998
- 1998-09-11 CA CA002302630A patent/CA2302630A1/en not_active Abandoned
- 1998-09-11 EP EP98942377A patent/EP1019404A4/en not_active Withdrawn
- 1998-09-11 ID IDW20000441A patent/ID26937A/id unknown
- 1998-09-11 JP JP2000510734A patent/JP2001515900A/ja not_active Withdrawn
- 1998-09-11 NZ NZ502994A patent/NZ502994A/en unknown
- 1998-09-11 KR KR1020007002574A patent/KR20010023890A/ko not_active Withdrawn
- 1998-09-11 WO PCT/AU1998/000748 patent/WO1999012927A1/en not_active Ceased
- 1998-09-11 CN CN98809019A patent/CN1269801A/zh active Pending

Also Published As

Publication number	Publication date
EP1019404A4 (en)	2001-07-04
ID26937A (id)	2001-02-22
JP2001515900A (ja)	2001-09-25
EP1019404A1 (en)	2000-07-19
KR20010023890A (ko)	2001-03-26
WO1999012927A1 (en)	1999-03-18
CN1269801A (zh)	2000-10-11
NZ502994A (en)	2001-12-21
AUPO912997A0 (en)	1997-10-02

Legal Events

Date	Code	Title	Description
2004-09-13	FZDE	Discontinued

Publication	Publication Date	Title
RU2067097C1 (ru)	1996-09-27	Способ получения дидезоксидидегидрокарбоциклических нуклеозидов
AU2007212648B2 (en)	2013-04-04	Inhibitors of E1 activating enzyme
EP0329348B1 (en)	1995-07-12	2',3'-Dideoxy-2',2'-difluoronucleosides
EA004983B1 (ru)	2004-10-28	Производные 2-аминокарбонил-9h-пурина
CA1276635C (en)	1990-11-20	9-(2-(hydroxymethyl)cycloalkylmethyl)guanines
CS203093B2 (en)	1981-02-27	Method of preparing substituted purines
SK18192001A3 (sk)	2003-04-01	Deriváty purínu
KR20120092153A (ko)	2012-08-20	바이러스 감염 치료를 위한 ２＇?플루오로?６＇?메틸렌 카보사이클릭 뉴클레오사이드 및 방법
JP2001509483A (ja)	2001-07-24	サイクリン依存性キナーゼ阻害性プリン誘導体
HU195657B (en)	1988-06-28	Process for production of carbocyclic pirin nucleorids and medical compounds containing them
WO1996002543A1 (en)	1996-02-01	2,3-dihydroxy cyclopentane derivatives of purines
MXPA97002488A (en)	1998-04-01	Compounds of purine and guanine as inhibitors of
CA2302630A1 (en)	1999-03-18	Purine acyclonucleosides as antiviral agents
HU203755B (en)	1991-09-30	Process for producing cyclopenentyl-purine derivatives and pharmaceutical compositions containing them
HUT59152A (en)	1992-04-28	Process for producing cyclic analogs of nucleosides and pharmaceutical compositions comprising same as active ingredient
JP2722215B2 (ja)	1998-03-04	新規なアリステロマイシン／アデノシン誘導体類
IE890953L (en)	1989-09-25	Novel acetylenic,cyano and allenic aristeromycin/adenosine derivatives
US20090270431A1 (en)	2009-10-29	Cyclopentenol Nucleoside Compounds Intermediates for their Synthesis and Methods of Treating Viral Infections
EP0242482A2 (en)	1987-10-28	Antiviral purine derivatives and process for their preparation
CA2944122A1 (en)	2015-09-03	Sialic acid derivatives
CA2098876A1 (en)	1993-12-23	2'-deoxy-2',2-'difluoro(2,6,8-substituted)purine nucleosides having anti-viral and anti-cancer activity and intermediates
CN1921867B (zh)	2010-05-05	用于治疗hiv感染的膦酸核苷衍生物
EP0366385B1 (en)	1993-06-09	Guanine derivatives having antiviral activity and their pharmaceutically acceptable salts
AU740264C (en)	2002-06-06	Antiviral agents
GB1569393A (en)	1980-06-11	Purine derivates