JPH11507390A - 経口活性なアデノシンキナーゼインヒビター - Google Patents

経口活性なアデノシンキナーゼインヒビター

Info

Publication number: JPH11507390A
Authority: JP; Japan
Prior art keywords: compound; phenyl; ribofuranosyl; deoxy; pyrimidine
Prior art date: 1995-06-07
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.): Ceased

Application number

JP9502318A

Other languages

English (en)

Japanese (ja)

Other versions

JPH11507390A5 (2

Inventor

ウガルカー，ビーマラオ・ジー

エリオン，マーク・ディ

ガレノ，ジョージ・イー・ゴメス

カステリーノ，アンジェロ・ジェイ

ブラウン，クリントン・イー

Original Assignee

ジェンシア・シコー

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.)

1995-06-07

Filing date

1996-06-07

Publication date

1999-06-29

1996-06-07 Application filed by ジェンシア・シコー filed Critical ジェンシア・シコー

1999-06-29 Publication of JPH11507390A publication Critical patent/JPH11507390A/ja

2004-07-29 Publication of JPH11507390A5 publication Critical patent/JPH11507390A5/ja

Status Ceased legal-status Critical Current

Links

239000003121 adenosine kinase inhibitor Substances 0.000 title abstract description 25
150000001875 compounds Chemical class 0.000 claims description 175
-1 hydroxy, amino Chemical group 0.000 claims description 95
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 73
229910052739 hydrogen Inorganic materials 0.000 claims description 45
239000001257 hydrogen Substances 0.000 claims description 44
125000003118 aryl group Chemical group 0.000 claims description 40
229910052736 halogen Inorganic materials 0.000 claims description 37
150000002367 halogens Chemical class 0.000 claims description 37
125000000217 alkyl group Chemical group 0.000 claims description 35
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 35
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 25
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 22
229910052757 nitrogen Chemical group 0.000 claims description 18
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 17
229910052799 carbon Inorganic materials 0.000 claims description 17
150000002431 hydrogen Chemical class 0.000 claims description 16
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 15
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 9
229910052731 fluorine Inorganic materials 0.000 claims description 9
239000011737 fluorine Substances 0.000 claims description 9
125000003545 alkoxy group Chemical group 0.000 claims description 8
125000003342 alkenyl group Chemical group 0.000 claims description 7
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 7
150000003839 salts Chemical class 0.000 claims description 7
125000003710 aryl alkyl group Chemical group 0.000 claims description 6
125000004093 cyano group Chemical group *C#N 0.000 claims description 6
125000000304 alkynyl group Chemical group 0.000 claims description 5
125000001153 fluoro group Chemical group F* 0.000 claims description 5
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
229940124530 sulfonamide Drugs 0.000 claims description 5
150000003456 sulfonamides Chemical class 0.000 claims description 5
LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical group NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 claims description 4
125000002252 acyl group Chemical group 0.000 claims description 3
125000004442 acylamino group Chemical group 0.000 claims description 3
150000003857 carboxamides Chemical class 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
150000001540 azides Chemical class 0.000 claims description 2
YDVJBLJCSLVMSY-UHFFFAOYSA-N carbamoyl cyanide Chemical compound NC(=O)C#N YDVJBLJCSLVMSY-UHFFFAOYSA-N 0.000 claims description 2
125000001188 haloalkyl group Chemical group 0.000 claims description 2
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 1
150000005676 cyclic carbonates Chemical class 0.000 claims 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 abstract description 89
239000002126 C01EB10 - Adenosine Substances 0.000 abstract description 43
229960005305 adenosine Drugs 0.000 abstract description 43
238000004519 manufacturing process Methods 0.000 abstract description 24
230000000694 effects Effects 0.000 abstract description 23
239000002777 nucleoside Substances 0.000 abstract description 14
230000001965 increasing effect Effects 0.000 abstract description 12
201000010099 disease Diseases 0.000 abstract description 8
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 8
150000003230 pyrimidines Chemical class 0.000 abstract description 8
230000004054 inflammatory process Effects 0.000 abstract description 7
239000002718 pyrimidine nucleoside Substances 0.000 abstract description 7
206010061218 Inflammation Diseases 0.000 abstract description 6
150000003833 nucleoside derivatives Chemical class 0.000 abstract description 6
208000026106 cerebrovascular disease Diseases 0.000 abstract description 2
230000002526 effect on cardiovascular system Effects 0.000 abstract description 2
208000024172 Cardiovascular disease Diseases 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 72
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 61
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 53
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 52
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 51
239000000203 mixture Substances 0.000 description 49
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 39
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 39
JJTNLWSCFYERCK-UHFFFAOYSA-N 7h-pyrrolo[2,3-d]pyrimidine Chemical compound N1=CN=C2NC=CC2=C1 JJTNLWSCFYERCK-UHFFFAOYSA-N 0.000 description 35
239000000243 solution Substances 0.000 description 33
238000000034 method Methods 0.000 description 31
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 29
239000000047 product Substances 0.000 description 23
230000002829 reductive effect Effects 0.000 description 23
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 19
241000700159 Rattus Species 0.000 description 19
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 19
OOXNYFKPOPJIOT-UHFFFAOYSA-N 5-(3-bromophenyl)-7-(6-morpholin-4-ylpyridin-3-yl)pyrido[2,3-d]pyrimidin-4-amine;dihydrochloride Chemical compound Cl.Cl.C=12C(N)=NC=NC2=NC(C=2C=NC(=CC=2)N2CCOCC2)=CC=1C1=CC=CC(Br)=C1 OOXNYFKPOPJIOT-UHFFFAOYSA-N 0.000 description 18
108010076278 Adenosine kinase Proteins 0.000 description 18
102100032534 Adenosine kinase Human genes 0.000 description 18
238000006243 chemical reaction Methods 0.000 description 18
238000002360 preparation method Methods 0.000 description 18
241001465754 Metazoa Species 0.000 description 17
239000004480 active ingredient Substances 0.000 description 17
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 16
238000009472 formulation Methods 0.000 description 16
230000005764 inhibitory process Effects 0.000 description 16
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
239000012071 phase Substances 0.000 description 15
239000007787 solid Substances 0.000 description 15
239000002904 solvent Substances 0.000 description 15
208000002193 Pain Diseases 0.000 description 13
125000000623 heterocyclic group Chemical group 0.000 description 13
239000011541 reaction mixture Substances 0.000 description 13
238000012360 testing method Methods 0.000 description 13
238000002347 injection Methods 0.000 description 12
239000007924 injection Substances 0.000 description 12
230000004044 response Effects 0.000 description 12
238000003756 stirring Methods 0.000 description 12
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 11
230000015572 biosynthetic process Effects 0.000 description 11
239000002244 precipitate Substances 0.000 description 11
150000004943 pyrrolo[2,3-d]pyrimidines Chemical class 0.000 description 11
239000000377 silicon dioxide Substances 0.000 description 11
239000000725 suspension Substances 0.000 description 11
238000003786 synthesis reaction Methods 0.000 description 11
239000003112 inhibitor Substances 0.000 description 10
239000003826 tablet Substances 0.000 description 10
QUKPALAWEPMWOS-UHFFFAOYSA-N 1h-pyrazolo[3,4-d]pyrimidine Chemical compound C1=NC=C2C=NNC2=N1 QUKPALAWEPMWOS-UHFFFAOYSA-N 0.000 description 9
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
210000002683 foot Anatomy 0.000 description 9
230000003389 potentiating effect Effects 0.000 description 9
WHSIXKUPQCKWBY-IOSLPCCCSA-N 5-iodotubercidin Chemical compound C1=C(I)C=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O WHSIXKUPQCKWBY-IOSLPCCCSA-N 0.000 description 8
206010010904 Convulsion Diseases 0.000 description 8
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 8
210000004369 blood Anatomy 0.000 description 8
239000008280 blood Substances 0.000 description 8
210000004027 cell Anatomy 0.000 description 8
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125000005842 heteroatom Chemical group 0.000 description 8
239000000651 prodrug Substances 0.000 description 8
229940002612 prodrug Drugs 0.000 description 8
235000000346 sugar Nutrition 0.000 description 8
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 7
239000002253 acid Substances 0.000 description 7
239000002585 base Substances 0.000 description 7
239000003054 catalyst Substances 0.000 description 7
238000004587 chromatography analysis Methods 0.000 description 7
238000001914 filtration Methods 0.000 description 7
235000003599 food sweetener Nutrition 0.000 description 7
239000003921 oil Substances 0.000 description 7
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 7
239000000741 silica gel Substances 0.000 description 7
229910002027 silica gel Inorganic materials 0.000 description 7
239000003765 sweetening agent Substances 0.000 description 7
RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 6
HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 6
XYEJDFIDVKWWTR-UHFFFAOYSA-N 2-amino-4-phenyl-1h-pyrrole-3-carbonitrile Chemical compound N#CC1=C(N)NC=C1C1=CC=CC=C1 XYEJDFIDVKWWTR-UHFFFAOYSA-N 0.000 description 6
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
241000282472 Canis lupus familiaris Species 0.000 description 6
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JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
230000006399 behavior Effects 0.000 description 6
230000009286 beneficial effect Effects 0.000 description 6
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239000002775 capsule Substances 0.000 description 6
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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 4
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125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 3
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CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
229940081974 saccharin Drugs 0.000 description 1
235000019204 saccharin Nutrition 0.000 description 1
239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
238000003345 scintillation counting Methods 0.000 description 1
238000012216 screening Methods 0.000 description 1
230000008313 sensitization Effects 0.000 description 1
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230000001568 sexual effect Effects 0.000 description 1
210000004927 skin cell Anatomy 0.000 description 1
239000002002 slurry Substances 0.000 description 1
150000003385 sodium Chemical class 0.000 description 1
235000010413 sodium alginate Nutrition 0.000 description 1
239000000661 sodium alginate Substances 0.000 description 1
229940005550 sodium alginate Drugs 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910001467 sodium calcium phosphate Inorganic materials 0.000 description 1
JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
239000001488 sodium phosphate Substances 0.000 description 1
229940080313 sodium starch Drugs 0.000 description 1
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239000007901 soft capsule Substances 0.000 description 1
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PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical compound [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
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239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
VPWFNCFRPQFWGS-UHFFFAOYSA-N tert-butyl n-[amino-[(2-methylpropan-2-yl)oxycarbonylamino]methylidene]carbamate Chemical compound CC(C)(C)OC(=O)NC(N)=NC(=O)OC(C)(C)C VPWFNCFRPQFWGS-UHFFFAOYSA-N 0.000 description 1
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GGUBFICZYGKNTD-UHFFFAOYSA-N triethyl phosphonoacetate Chemical compound CCOC(=O)CP(=O)(OCC)OCC GGUBFICZYGKNTD-UHFFFAOYSA-N 0.000 description 1
210000003901 trigeminal nerve Anatomy 0.000 description 1
230000001960 triggered effect Effects 0.000 description 1
POSZUTFLHGNLHX-KSBRXOFISA-N tris maleate Chemical compound OCC(N)(CO)CO.OCC(N)(CO)CO.OC(=O)\C=C/C(O)=O POSZUTFLHGNLHX-KSBRXOFISA-N 0.000 description 1
RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
231100000397 ulcer Toxicity 0.000 description 1
150000003673 urethanes Chemical class 0.000 description 1
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238000003260 vortexing Methods 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
- A61K31/7052—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides
- A61K31/706—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom
- A61K31/7064—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
- A61K31/7052—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides
- A61K31/706—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom
- A61K31/7064—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines
- A61K31/7076—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines containing purines, e.g. adenosine, adenylic acid
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/052—Imidazole radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/06—Pyrimidine radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/14—Pyrrolo-pyrimidine radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/16—Purine radicals

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Molecular Biology (AREA)
Engineering & Computer Science (AREA)
Biochemistry (AREA)
Medicinal Chemistry (AREA)
Biotechnology (AREA)
Pharmacology & Pharmacy (AREA)
Genetics & Genomics (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Epidemiology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Bioinformatics & Cheminformatics (AREA)
Pain & Pain Management (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Rheumatology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Saccharide Compounds (AREA)

JP9502318A 1995-06-07 1996-06-07 経口活性なアデノシンキナーゼインヒビター Ceased JPH11507390A (ja)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US473,491		1995-06-07
US08/473,491 US5721356A (en)	1989-09-15	1995-06-07	Orally active adenosine kinase inhibitors
PCT/US1996/010919 WO1996040706A1 (en)	1995-06-07	1996-06-07	Orally active adenosine kinase inhibitors

Publications (2)

Publication Number	Publication Date
JPH11507390A true JPH11507390A (ja)	1999-06-29
JPH11507390A5 JPH11507390A5 (2)	2004-07-29

Family

ID=23879751

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP9502318A Ceased JPH11507390A (ja)	1995-06-07	1996-06-07	経口活性なアデノシンキナーゼインヒビター

Country Status (10)

Country	Link
US (1)	US5721356A (2)
EP (1)	EP0832092B1 (2)
JP (1)	JPH11507390A (2)
AT (1)	ATE282628T1 (2)
AU (1)	AU6395896A (2)
BR (1)	BR9608625A (2)
CA (1)	CA2247984A1 (2)
DE (1)	DE69633860T2 (2)
IL (1)	IL122334A0 (2)
WO (1)	WO1996040706A1 (2)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP2005501122A (ja) *	2001-08-22	2005-01-13	バイエル・ヘルスケア・アクチェンゲゼルシャフト	新規４−アミノフロピリミジン化合物およびそれらの使用
JP2008520744A (ja) *	2004-11-19	2008-06-19	ザ・レジェンツ・オブ・ザ・ユニバーシティ・オブ・カリフォルニア	抗炎症性ピラゾロピリミジン
US9629843B2 (en)	2008-07-08	2017-04-25	The Regents Of The University Of California	MTOR modulators and uses thereof

Families Citing this family (58)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US7772432B2 (en)	1991-09-19	2010-08-10	Astrazeneca Ab	Amidobenzamide derivatives which are useful as cytokine inhibitors
US7863444B2 (en)	1997-03-19	2011-01-04	Abbott Laboratories	4-aminopyrrolopyrimidines as kinase inhibitors
US7462605B2 (en)	1998-01-23	2008-12-09	Celmed Oncology (Usa), Inc.	Phosphoramidate compounds and methods of use
US6713474B2 (en)	1998-09-18	2004-03-30	Abbott Gmbh & Co. Kg	Pyrrolopyrimidines as therapeutic agents
GB9906566D0 (en) *	1999-03-23	1999-05-19	Zeneca Ltd	Chemical compounds
US7071199B1 (en)	1999-09-17	2006-07-04	Abbott Gmbh & Cco. Kg	Kinase inhibitors as therapeutic agents
CA2385747A1 (en)	1999-09-17	2001-03-22	Gavin C. Hirst	Pyrazolopyrimidines as therapeutic agents
DE10042092A1 (de) *	2000-08-26	2002-03-07	Dresden Arzneimittel	Antikonvulsiv wirkende 2,5-Dihydro-pyrazolo(3,4-d)pyrimidin-4-one und Verfahren zu deren Darstellung
JP2007500245A (ja) *	2003-06-10	2007-01-11	スミスクラインビーチャムコーポレーション	化合物
BRPI0400869B8 (pt) *	2004-03-02	2021-05-25	Univ Estadual Campinas Unicamp	novos compostos derivados de 4-anilinoquinazolinas com propriedade inibidora de adenosinacinases
RS52458B (sr)	2005-02-04	2013-02-28	Millennium Pharmaceuticals Inc.	Inhibitori e1 aktivirajućih enzima
EA024006B1 (ru)	2006-02-02	2016-08-31	Миллениум Фармасьютикалз, Инк.	Ингибиторы е1 активирующих ферментов
WO2007114926A2 (en)	2006-04-04	2007-10-11	The Regents Of The University Of California	Kinase antagonists
GB2467670B (en)	2007-10-04	2012-08-01	Intellikine Inc	Chemical entities and therapeutic uses thereof
US8193182B2 (en)	2008-01-04	2012-06-05	Intellikine, Inc.	Substituted isoquinolin-1(2H)-ones, and methods of use thereof
EP3613743B1 (en)	2008-01-04	2022-03-16	Intellikine, LLC	Processes for the preparation of 1h-pyrazolo[3,4-d]pyrimidin-4-amine derivatives
US8993580B2 (en)	2008-03-14	2015-03-31	Intellikine Llc	Benzothiazole kinase inhibitors and methods of use
US8637542B2 (en)	2008-03-14	2014-01-28	Intellikine, Inc.	Kinase inhibitors and methods of use
JP5788316B2 (ja)	2008-07-08	2015-09-30	インテリカイン，エルエルシー	キナーゼインヒビターおよび使用方法
US8703778B2 (en)	2008-09-26	2014-04-22	Intellikine Llc	Heterocyclic kinase inhibitors
WO2010045542A2 (en)	2008-10-16	2010-04-22	The Regents Of The University Of California	Fused ring heteroaryl kinase inhibitors
US8476431B2 (en)	2008-11-03	2013-07-02	Itellikine LLC	Benzoxazole kinase inhibitors and methods of use
EP2427195B1 (en)	2009-05-07	2019-05-01	Intellikine, LLC	Heterocyclic compounds and uses thereof
EP2430026A1 (en)	2009-05-14	2012-03-21	Millennium Pharmaceuticals, Inc.	Hydrochloride salt of ((1s,2s,4r)-4-{4-[(1s)-2,3-dihydro-1h-inden-1-ylamino]-7h-pyrrolo [2,3-d]pyrimidin-7-yl}-2-hydroxycyclopentyl)methyl sulfamate
PE20121148A1 (es)	2009-08-17	2012-09-07	Intellikine Llc	Compuestos heterociclicos y usos de los mismos
US8980899B2 (en)	2009-10-16	2015-03-17	The Regents Of The University Of California	Methods of inhibiting Ire1
CA2799579A1 (en)	2010-05-21	2011-11-24	Intellikine, Inc.	Chemical compounds, compositions and methods for kinase modulation
JP2013545749A (ja)	2010-11-10	2013-12-26	インフィニティーファーマシューティカルズ，インコーポレイテッド	複素環化合物及びその使用
TWI674262B (zh)	2011-01-10	2019-10-11	美商英菲尼提製藥股份有限公司	製備異喹啉酮之方法及異喹啉酮之固體形式
US9295673B2 (en)	2011-02-23	2016-03-29	Intellikine Llc	Combination of mTOR inhibitors and P13-kinase inhibitors, and uses thereof
WO2013012915A1 (en)	2011-07-19	2013-01-24	Infinity Pharmaceuticals Inc.	Heterocyclic compounds and uses thereof
MX2014000648A (es)	2011-07-19	2014-09-25	Infinity Pharmaceuticals Inc	Compuestos heterociclicos y sus usos.
KR20140075693A (ko)	2011-08-29	2014-06-19	인피니티 파마슈티칼스, 인코포레이티드	헤테로사이클릭 화합물 및 그의 용도
MX370814B (es)	2011-09-02	2020-01-08	Univ California	Pirazolo[3,4-d]pirimidinas sustituidas y usos de las mismas.
US8940742B2 (en)	2012-04-10	2015-01-27	Infinity Pharmaceuticals, Inc.	Heterocyclic compounds and uses thereof
US8828998B2 (en)	2012-06-25	2014-09-09	Infinity Pharmaceuticals, Inc.	Treatment of lupus, fibrotic conditions, and inflammatory myopathies and other disorders using PI3 kinase inhibitors
WO2014001973A1 (en) *	2012-06-29	2014-01-03	Pfizer Inc.	NOVEL 4-(SUBSTITUTED-AMINO)-7H-PYRROLO[2,3-d]PYRIMIDINES AS LRRK2 INHIBITORS
MX2015003874A (es)	2012-09-26	2015-12-16	Univ California	Modulacion de ire1.
EP2914296B2 (en)	2012-11-01	2021-09-29	Infinity Pharmaceuticals, Inc.	Treatment of cancers using pi3 kinase isoform modulators
US9481667B2 (en)	2013-03-15	2016-11-01	Infinity Pharmaceuticals, Inc.	Salts and solid forms of isoquinolinones and composition comprising and methods of using the same
WO2014153509A1 (en)	2013-03-22	2014-09-25	Millennium Pharmaceuticals, Inc.	Combination of catalytic mtorc 1/2 inhibitors and selective inhibitors of aurora a kinase
WO2015051241A1 (en)	2013-10-04	2015-04-09	Infinity Pharmaceuticals, Inc.	Heterocyclic compounds and uses thereof
MX2021012208A (es)	2013-10-04	2023-01-19	Infinity Pharmaceuticals Inc	Compuestos heterocíclicos y usos de los mismos.
JP6487921B2 (ja)	2013-12-17	2019-03-20	ファイザー・インク	ＬＲＲＫ２阻害薬としての新規の３，４−二置換−１Ｈ−ピロロ［２，３−ｂ］ピリジンおよび４，５−二置換−７Ｈ−ピロロ［２，３−ｃ］ピリダジン
NZ724368A (en)	2014-03-19	2023-07-28	Infinity Pharmaceuticals Inc	Heterocyclic compounds for use in the treatment of pi3k-gamma mediated disorders
WO2015160975A2 (en)	2014-04-16	2015-10-22	Infinity Pharmaceuticals, Inc.	Combination therapies
WO2016054491A1 (en)	2014-10-03	2016-04-07	Infinity Pharmaceuticals, Inc.	Heterocyclic compounds and uses thereof
EA201890454A1 (ru)	2015-08-06	2018-07-31	Чимерикс, Инк.	Пирролопиримидиновые нуклеозиды и их аналоги, которые можно использовать в качестве противовирусных средств
EP4585268A3 (en)	2015-09-14	2025-10-15	Twelve Therapeutics, Inc.	Solid forms of isoquinolinone derivatives, process of making, compositions comprising, and methods of using the same
KR102161364B1 (ko)	2015-09-14	2020-09-29	화이자 인코포레이티드	LRRK2 억제제로서 이미다조[4,5-c]퀴놀린 및 이미다조[4,5-c][1,5]나프티리딘 유도체
US10759806B2 (en)	2016-03-17	2020-09-01	Infinity Pharmaceuticals, Inc.	Isotopologues of isoquinolinone and quinazolinone compounds and uses thereof as PI3K kinase inhibitors
WO2017214269A1 (en)	2016-06-08	2017-12-14	Infinity Pharmaceuticals, Inc.	Heterocyclic compounds and uses thereof
RU2754507C2 (ru)	2016-06-24	2021-09-02	Инфинити Фармасьютикалз, Инк.	Комбинированная терапия
WO2018195397A2 (en)	2017-04-21	2018-10-25	Kyn Therapeutics	Indole ahr inhibitors and uses thereof
WO2019060692A1 (en)	2017-09-21	2019-03-28	Chimerix, Inc.	MORPHIC FORMS OF 4-AMINO-7- (3,4-DIHYDROXY-5- (HYDROXYMETHYL) -ETRAHYDROFURAN-2-YL) -2-METHYL-7H-PYRROLO [2,3-D] PYRIMIDINE-5-CARBOXAMIDE AND THEIR USES
CN113194752A (zh)	2018-06-01	2021-07-30	康奈尔大学	Pi3k相关疾病或病症的组合疗法
US20220144839A1 (en) *	2018-10-16	2022-05-12	Ikena Oncology, Inc.	Indole ahr inhibitors and uses thereof
PT4065582T (pt)	2019-11-26	2025-05-22	Ikena Oncology Inc	Derivados polimórficos do carbazol e utilizações dos mesmos

Citations (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0496617A1 (en) *	1991-01-23	1992-07-29	Gensia, Inc.	Adenosine kinase inhibitors
WO1994017803A1 (en) *	1993-02-03	1994-08-18	Gensia, Inc.	Adenosine kinase inhibitors
WO1994018215A1 (en) *	1993-02-03	1994-08-18	Gensia, Inc.	Adenosine kinase inhibitors comprising lyxofuranosyl derivatives

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3309358A (en) *	1965-09-20	1967-03-14	Upjohn Co	7-deazaadenine 2', 5'-and 3', 5'-dinucleoside phosphate and process therefor
US3962211A (en) *	1975-01-13	1976-06-08	The University Of Utah	7-substituted nucleoside compounds
US4352795A (en) *	1981-01-29	1982-10-05	Warner-Lambert Company	7-β-D-Arabinofuranosyl-7H-pyrrolo[2,3-d]pyrimidine compounds and methods for their production
US4439604A (en) *	1981-01-29	1984-03-27	Warner-Lambert Company	7-β-D-Arabinofuranosyl-7H-pyrrolo[2,3-d]pyrimidine compounds and methods for their production
US4455420A (en) *	1983-01-13	1984-06-19	Hoffmann-La Roche Inc.	4-Amino-7-(5-deoxy-beta-D-ribofuranosyl)-5-iodo-7H-pyrrolo[2,3-d] pyrimidine
DE3739366A1 (de) *	1987-04-10	1988-10-27	Boehringer Mannheim Gmbh	Desaza-purin-nucleosid-derivate, verfahren zu deren herstellung sowie deren verwendung bei der nucleinsaeure-sequenzierung sowie als antivirale mittel
DE3712735A1 (de) *	1987-04-15	1988-11-10	Boehringer Mannheim Gmbh	Neue pyrazolo(3,4-d)pyrimidine, verfahren zu ihrer herstellung und verwendung als arzneimittel
WO1990003370A1 (en) *	1988-09-28	1990-04-05	Microprobe Corporation	DERIVATIVES OF PYRAZOLO[3,4-d]PYRIMIDINE
DE3924424A1 (de) *	1989-07-24	1991-01-31	Boehringer Mannheim Gmbh	Nucleosid-derivate, verfahren zu deren herstellung, deren verwendung als arzneimittel sowie deren verwendung bei der nucleinsaeure-sequenzierung
DE3931557A1 (de) *	1989-09-22	1991-04-04	Boehringer Mannheim Gmbh	Neue 2',3'-anhydro-nukleoside, verfahren zu deren herstellung sowie arzneimittel, die diese verbindungen enthalten
US6143749A (en) *	1995-06-07	2000-11-07	Abbott Laboratories	Heterocyclic substituted cyclopentane compounds

1995
- 1995-06-07 US US08/473,491 patent/US5721356A/en not_active Expired - Fee Related
1996
- 1996-06-07 AU AU63958/96A patent/AU6395896A/en not_active Abandoned
- 1996-06-07 EP EP96923451A patent/EP0832092B1/en not_active Expired - Lifetime
- 1996-06-07 IL IL12233496A patent/IL122334A0/xx unknown
- 1996-06-07 JP JP9502318A patent/JPH11507390A/ja not_active Ceased
- 1996-06-07 DE DE69633860T patent/DE69633860T2/de not_active Expired - Fee Related
- 1996-06-07 AT AT96923451T patent/ATE282628T1/de not_active IP Right Cessation
- 1996-06-07 WO PCT/US1996/010919 patent/WO1996040706A1/en not_active Ceased
- 1996-06-07 BR BR9608625-4A patent/BR9608625A/pt unknown
- 1996-06-07 CA CA002247984A patent/CA2247984A1/en not_active Abandoned

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0496617A1 (en) *	1991-01-23	1992-07-29	Gensia, Inc.	Adenosine kinase inhibitors
WO1994017803A1 (en) *	1993-02-03	1994-08-18	Gensia, Inc.	Adenosine kinase inhibitors
WO1994018215A1 (en) *	1993-02-03	1994-08-18	Gensia, Inc.	Adenosine kinase inhibitors comprising lyxofuranosyl derivatives

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP2005501122A (ja) *	2001-08-22	2005-01-13	バイエル・ヘルスケア・アクチェンゲゼルシャフト	新規４−アミノフロピリミジン化合物およびそれらの使用
JP2008520744A (ja) *	2004-11-19	2008-06-19	ザ・レジェンツ・オブ・ザ・ユニバーシティ・オブ・カリフォルニア	抗炎症性ピラゾロピリミジン
JP2015003926A (ja) *	2004-11-19	2015-01-08	ザリージェンツオブザユニバーシティオブカリフォルニア	抗炎症性ピラゾロピリミジン
US9512125B2 (en)	2004-11-19	2016-12-06	The Regents Of The University Of California	Substituted pyrazolo[3.4-D] pyrimidines as anti-inflammatory agents
US9629843B2 (en)	2008-07-08	2017-04-25	The Regents Of The University Of California	MTOR modulators and uses thereof

Also Published As

Publication number	Publication date
CA2247984A1 (en)	1996-12-19
EP0832092A1 (en)	1998-04-01
DE69633860T2 (de)	2005-11-10
US5721356A (en)	1998-02-24
WO1996040706A1 (en)	1996-12-19
IL122334A0 (en)	1998-04-05
EP0832092B1 (en)	2004-11-17
AU6395896A (en)	1996-12-30
ATE282628T1 (de)	2004-12-15
DE69633860D1 (en)	2004-12-23
BR9608625A (pt)	1999-12-07
MX9709773A (es)	1998-10-31

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Publication	Publication Date	Title
JPH11507390A (ja)	1999-06-29	経口活性なアデノシンキナーゼインヒビター
US5763597A (en)	1998-06-09	Orally active adenosine kinase inhibitors
US5726302A (en)	1998-03-10	Water soluble adenosine kinase inhibitors
US5795977A (en)	1998-08-18	Water soluble adenosine kinase inhibitors
CA2264155C (en)	2003-11-18	N6 heterocyclic substituted adenosine derivatives
EP0832091B1 (en)	2004-01-14	C-4' modified adenosine kinase inhibitors
US5646128A (en)	1997-07-08	Methods for treating adenosine kinase related conditions
EP0496617B1 (en)	1999-12-01	Adenosine kinase inhibitors
JPH08506343A (ja)	1996-07-09	リキソフラノシル誘導体を含むアデノシンキナーゼ阻害物質
WO1994017803A9 (en)	1994-09-29	Adenosine kinase inhibitors
AU1359992A (en)	1992-08-27	Adenosine kinase inhibitors
JP2009102366A (ja)	2009-05-14	Ａｉｃａリボシド類縁体
US5864033A (en)	1999-01-26	Adenosine kinase inhibitors
JP2001520655A (ja)	2001-10-30	５，７−ジ置換４−アミノピリド［２，３−ｄ］ピリミジン化合物およびアデノシンキナーゼ阻害剤としてのその用途
MXPA97009773A (en)	1999-01-11	Inhibitors of adenosin cinasa oralmente acti
MXPA97009656A (en)	1999-01-11	Soluble adenosin kinase inhibitors in a
IE920190A1 (en)	1992-07-29	Adenosine kinase inhibitors