NO320854B1 - Heterocykliske, subsitituerte adenosinderivater, farmasoytiske preparater omfattende slike og anvendelse av derivatene for fremstilling av farmasoytiske preparater - Google Patents

Heterocykliske, subsitituerte adenosinderivater, farmasoytiske preparater omfattende slike og anvendelse av derivatene for fremstilling av farmasoytiske preparater Download PDF

Info

Publication number: NO320854B1
Authority: NO; Norway
Prior art keywords: compound; alkyl; amino; group; methyl
Prior art date: 1999-05-24

Application number

NO20015662A

Other languages

English (en)

Norwegian (no)

Other versions

NO20015662D0 (no

NO20015662L (no

Inventor

Lisa Wang

Jeff A Zablocki

Venkata P Palle

Brent K Blackburn

Chris Melville

Elfatih O Elzein

Original Assignee

Cv Therapeutics 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.)

1999-05-24

Filing date

2001-11-20

Publication date

2006-02-06

2001-11-20 Application filed by Cv Therapeutics Inc filed Critical Cv Therapeutics Inc

2001-11-20 Publication of NO20015662D0 publication Critical patent/NO20015662D0/no

2002-01-23 Publication of NO20015662L publication Critical patent/NO20015662L/no

2006-02-06 Publication of NO320854B1 publication Critical patent/NO320854B1/no

Links

239000000825 pharmaceutical preparation Substances 0.000 title claims description 16
238000002360 preparation method Methods 0.000 title claims description 7
150000003835 adenosine derivatives Chemical class 0.000 title description 5
125000000623 heterocyclic group Chemical group 0.000 title description 5
239000008194 pharmaceutical composition Chemical class 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 80
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 21
-1 1-amino-3-methylpropyl Chemical group 0.000 claims description 19
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 claims description 10
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
241000124008 Mammalia Species 0.000 claims description 7
239000002126 C01EB10 - Adenosine Substances 0.000 claims description 6
229960005305 adenosine Drugs 0.000 claims description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
229940044551 receptor antagonist Drugs 0.000 claims description 6
239000002464 receptor antagonist Substances 0.000 claims description 6
206010003658 Atrial Fibrillation Diseases 0.000 claims description 5
206010003662 Atrial flutter Diseases 0.000 claims description 5
208000003734 Supraventricular Tachycardia Diseases 0.000 claims description 5
239000003937 drug carrier Substances 0.000 claims description 5
239000000546 pharmaceutical excipient Substances 0.000 claims description 5
125000004076 pyridyl group Chemical group 0.000 claims description 5
101150007969 ADORA1 gene Proteins 0.000 claims description 4
208000001871 Tachycardia Diseases 0.000 claims description 4
125000000217 alkyl group Chemical group 0.000 claims description 4
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
125000000753 cycloalkyl group Chemical group 0.000 claims description 4
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
230000006794 tachycardia Effects 0.000 claims description 4
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 3
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
125000005475 oxolanyl group Chemical group 0.000 claims description 2
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 33
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 32
229940125904 compound 1 Drugs 0.000 description 28
125000002887 hydroxy group Chemical group [H]O* 0.000 description 25
238000005481 NMR spectroscopy Methods 0.000 description 22
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
229940125782 compound 2 Drugs 0.000 description 19
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
230000000694 effects Effects 0.000 description 18
239000000126 substance Substances 0.000 description 18
239000000243 solution Substances 0.000 description 17
241000700159 Rattus Species 0.000 description 16
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 16
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 16
WREOTYWODABZMH-DTZQCDIJSA-N [[(2r,3s,4r,5r)-3,4-dihydroxy-5-[2-oxo-4-(2-phenylethoxyamino)pyrimidin-1-yl]oxolan-2-yl]methoxy-hydroxyphosphoryl] phosphono hydrogen phosphate Chemical compound O[C@@H]1[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)O[C@H]1N(C=C\1)C(=O)NC/1=N\OCCC1=CC=CC=C1 WREOTYWODABZMH-DTZQCDIJSA-N 0.000 description 14
229940125758 compound 15 Drugs 0.000 description 14
150000002148 esters Chemical class 0.000 description 14
238000003818 flash chromatography Methods 0.000 description 14
239000013543 active substance Substances 0.000 description 13
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238000006243 chemical reaction Methods 0.000 description 13
239000000651 prodrug Substances 0.000 description 13
229940002612 prodrug Drugs 0.000 description 13
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
239000000543 intermediate Substances 0.000 description 12
238000000034 method Methods 0.000 description 12
125000004545 purin-9-yl group Chemical group N1=CN=C2N(C=NC2=C1)* 0.000 description 12
230000036470 plasma concentration Effects 0.000 description 11
230000033764 rhythmic process Effects 0.000 description 11
JBDSSBMEKXHSJF-UHFFFAOYSA-N cyclopentanecarboxylic acid Chemical group OC(=O)C1CCCC1 JBDSSBMEKXHSJF-UHFFFAOYSA-N 0.000 description 10
IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 8
125000004185 ester group Chemical group 0.000 description 8
239000000203 mixture Substances 0.000 description 8
235000019260 propionic acid Nutrition 0.000 description 8
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 8
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 7
235000002639 sodium chloride Nutrition 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 6
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 6
ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
101100284355 Rattus norvegicus Hr gene Proteins 0.000 description 5
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 5
230000009471 action Effects 0.000 description 5
238000010586 diagram Methods 0.000 description 5
238000001704 evaporation Methods 0.000 description 5
230000008020 evaporation Effects 0.000 description 5
LSACYLWPPQLVSM-UHFFFAOYSA-N isobutyric acid anhydride Chemical group CC(C)C(=O)OC(=O)C(C)C LSACYLWPPQLVSM-UHFFFAOYSA-N 0.000 description 5
108020003175 receptors Proteins 0.000 description 5
102000005962 receptors Human genes 0.000 description 5
150000003839 salts Chemical class 0.000 description 5
239000007787 solid Substances 0.000 description 5
239000002904 solvent Substances 0.000 description 5
238000004809 thin layer chromatography Methods 0.000 description 5
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
101150041968 CDC13 gene Proteins 0.000 description 4
YZGQDNOIGFBYKF-UHFFFAOYSA-N Ethoxyacetic acid Chemical group CCOCC(O)=O YZGQDNOIGFBYKF-UHFFFAOYSA-N 0.000 description 4
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 4
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
238000001727 in vivo Methods 0.000 description 4
239000007788 liquid Substances 0.000 description 4
PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 4
239000000047 product Substances 0.000 description 4
229910052938 sodium sulfate Inorganic materials 0.000 description 4
235000011152 sodium sulphate Nutrition 0.000 description 4
239000007858 starting material Substances 0.000 description 4
230000002194 synthesizing effect Effects 0.000 description 4
230000001225 therapeutic effect Effects 0.000 description 4
108050000203 Adenosine receptors Proteins 0.000 description 3
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XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 description 3
OPFJDXRVMFKJJO-ZHHKINOHSA-N N-{[3-(2-benzamido-4-methyl-1,3-thiazol-5-yl)-pyrazol-5-yl]carbonyl}-G-dR-G-dD-dD-dD-NH2 Chemical compound S1C(C=2NN=C(C=2)C(=O)NCC(=O)N[C@H](CCCN=C(N)N)C(=O)NCC(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(N)=O)=C(C)N=C1NC(=O)C1=CC=CC=C1 OPFJDXRVMFKJJO-ZHHKINOHSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
239000000969 carrier Substances 0.000 description 3
150000001768 cations Chemical class 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
229940126086 compound 21 Drugs 0.000 description 3
238000010511 deprotection reaction Methods 0.000 description 3
150000005690 diesters Chemical class 0.000 description 3
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AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 3
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WWTBZEKOSBFBEM-SPWPXUSOSA-N (2s)-2-[[2-benzyl-3-[hydroxy-[(1r)-2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]phosphoryl]propanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound N([C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)O)C(=O)C(CP(O)(=O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1C=CC=CC=1)CC1=CC=CC=C1 WWTBZEKOSBFBEM-SPWPXUSOSA-N 0.000 description 2
CANZBRDGRHNSGZ-NSHDSACASA-N (2s)-3-methyl-2-(phenylmethoxycarbonylamino)butanoic acid Chemical compound CC(C)[C@@H](C(O)=O)NC(=O)OCC1=CC=CC=C1 CANZBRDGRHNSGZ-NSHDSACASA-N 0.000 description 2
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VYQNWZOUAUKGHI-UHFFFAOYSA-N monobenzone Chemical compound C1=CC(O)=CC=C1OCC1=CC=CC=C1 VYQNWZOUAUKGHI-UHFFFAOYSA-N 0.000 description 1
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
239000004006 olive oil Substances 0.000 description 1
235000008390 olive oil Nutrition 0.000 description 1
150000002923 oximes Chemical class 0.000 description 1
DIRLDPKYOATBIA-UHFFFAOYSA-N oxolan-3-yl acetate Chemical compound CC(=O)OC1CCOC1 DIRLDPKYOATBIA-UHFFFAOYSA-N 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
239000001814 pectin Substances 0.000 description 1
235000010987 pectin Nutrition 0.000 description 1
229920001277 pectin Polymers 0.000 description 1
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical group OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
230000035790 physiological processes and functions Effects 0.000 description 1
230000006461 physiological response Effects 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
239000002243 precursor Substances 0.000 description 1
230000008569 process Effects 0.000 description 1
102000004196 processed proteins & peptides Human genes 0.000 description 1
108090000765 processed proteins & peptides Proteins 0.000 description 1
235000019833 protease Nutrition 0.000 description 1
239000000296 purinergic P1 receptor antagonist Substances 0.000 description 1
238000011084 recovery Methods 0.000 description 1
230000009467 reduction Effects 0.000 description 1
230000036279 refractory period Effects 0.000 description 1
230000002441 reversible effect Effects 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
239000001509 sodium citrate Substances 0.000 description 1
NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
238000000638 solvent extraction Methods 0.000 description 1
238000013223 sprague-dawley female rat Methods 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
230000004936 stimulating effect Effects 0.000 description 1
239000011550 stock solution Substances 0.000 description 1
239000001384 succinic acid Substances 0.000 description 1
238000013268 sustained release Methods 0.000 description 1
239000012730 sustained-release form Substances 0.000 description 1
230000002889 sympathetic effect Effects 0.000 description 1
230000009885 systemic effect Effects 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
230000002110 toxicologic effect Effects 0.000 description 1
231100000759 toxicological effect Toxicity 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
238000003828 vacuum filtration Methods 0.000 description 1
229960004295 valine Drugs 0.000 description 1

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
- C07H19/16—Purine radicals
- C07H19/167—Purine radicals with ribosyl as the saccharide radical
- 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
- 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
- A61K31/7048—Compounds having saccharide radicals and heterocyclic rings having oxygen as a ring hetero atom, e.g. leucoglucosan, hesperidin, erythromycin, nystatin, digitoxin or digoxin
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
General Health & Medical Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Molecular Biology (AREA)
Cardiology (AREA)
Biochemistry (AREA)
Biotechnology (AREA)
Genetics & Genomics (AREA)
Heart & Thoracic Surgery (AREA)
Urology & Nephrology (AREA)
Vascular Medicine (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Saccharide Compounds (AREA)
Medicinal Preparation (AREA)

NO20015662A 1999-05-24 2001-11-20 Heterocykliske, subsitituerte adenosinderivater, farmasoytiske preparater omfattende slike og anvendelse av derivatene for fremstilling av farmasoytiske preparater NO320854B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US09/317,523 US6576619B2 (en)	1999-05-24	1999-05-24	Orally active A1 adenosine receptor agonists
PCT/US2000/014036 WO2000071558A1 (en)	1999-05-24	2000-05-19	Orally active a1 adenosine receptor agonists

Publications (3)

Publication Number	Publication Date
NO20015662D0 NO20015662D0 (no)	2001-11-20
NO20015662L NO20015662L (no)	2002-01-23
NO320854B1 true NO320854B1 (no)	2006-02-06

Family

ID=23234062

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO20015662A NO320854B1 (no)	1999-05-24	2001-11-20	Heterocykliske, subsitituerte adenosinderivater, farmasoytiske preparater omfattende slike og anvendelse av derivatene for fremstilling av farmasoytiske preparater

Country Status (19)

Country	Link
US (1)	US6576619B2 (de)
EP (1)	EP1181302B1 (de)
JP (2)	JP2003520776A (de)
KR (1)	KR100537032B1 (de)
CN (1)	CN1183153C (de)
AR (1)	AR035909A1 (de)
AT (1)	ATE250621T1 (de)
AU (1)	AU760658B2 (de)
BR (1)	BR0010882A (de)
CA (1)	CA2375040C (de)
DE (1)	DE60005507T2 (de)
ES (1)	ES2206238T3 (de)
IL (2)	IL146471A0 (de)
MX (1)	MXPA01012038A (de)
NO (1)	NO320854B1 (de)
NZ (1)	NZ515580A (de)
TW (1)	TW593330B (de)
WO (1)	WO2000071558A1 (de)
ZA (1)	ZA200109626B (de)

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IL127947A0 (en)	1999-01-07	1999-11-30	Can Fite Technologies Ltd	Pharmaceutical use of adenosine agonists
US6790839B2 (en)	1999-01-07	2004-09-14	Can-Fite Biopharma Ltd.	Pharmaceutical administration of adenosine agonists
WO2003070739A1 (en) *	2002-02-19	2003-08-28	Cv Therapeutics, Inc.	Partial and full agonists of a1 adenosine receptors
US20040028729A1 (en) *	2002-04-29	2004-02-12	Shojaei Amir H.	Pharmaceutical formulations with improved bioavailability
US8709476B2 (en)	2003-11-04	2014-04-29	Supernus Pharmaceuticals, Inc.	Compositions of quaternary ammonium compounds containing bioavailability enhancers
DE602004030931D1 (de) *	2003-11-04	2011-02-17	Supernus Pharmaceuticals Inc
CN101479268B (zh)	2006-06-27	2012-08-08	Cbt发展有限公司	2-0’-甲基腺苷衍生物及其用作制备腺苷受体的激动剂或拮抗剂的应用
US7731604B2 (en) *	2006-10-31	2010-06-08	Taylor Made Golf Company, Inc.	Golf club iron head
CN101712709A (zh) *	2008-10-06	2010-05-26	中国医学科学院药物研究所	三乙酰基-3-羟基苯基腺苷及其调血脂的用途
DE102011005232A1 (de)	2011-03-08	2012-09-13	AristoCon GmbH & Co. KG	Adenosin und seine Derivate zur Verwendung in der Schmerztherapie
MX2022002897A (es)	2019-09-11	2022-05-16	Scripps Research Inst	Profarmacos antivirales y formulaciones de los mismos.

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JPS57171998A (en)	1981-04-15	1982-10-22	Fujisawa Pharmaceut Co Ltd	Adenosine derivative and its salt, preparation thereof and medicinal composition containing the same
DE3138397A1 (de)	1981-09-26	1983-04-07	Hoechst Ag, 6230 Frankfurt	"arzneimittel, darin enthaltene vicinale dihydroxyalkylxanthine und herstellungsverfahren fuer diese xanthinverbindungen"
CA1255297A (en)	1984-10-26	1989-06-06	Bharat Trivedi	N.sup.6-benzopyrano and benzothiopyrano adenosines
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US4980379A (en)	1988-06-30	1990-12-25	The University Of Virginia	Use of adenosine antagonists in the treatment of bradyarrhythmias and hemodynamic depression associated with cardiopulmonary resucitation and/or cardiovascular collapse
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KR910700253A (ko)	1989-01-31	1991-03-14	로버트 제이, 바란	N_6-치환-9-메틸아데닌: 신규한 부류의 아데노신 수용체 길항질
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US5789416B1 (en) *	1996-08-27	1999-10-05	Cv Therapeutics Inc	N6 mono heterocyclic substituted adenosine derivatives
GB9723566D0 (en) *	1997-11-08	1998-01-07	Glaxo Group Ltd	Chemical compounds
GB9723590D0 (en) *	1997-11-08	1998-01-07	Glaxo Group Ltd	Chemical compounds

1999
- 1999-05-24 US US09/317,523 patent/US6576619B2/en not_active Expired - Lifetime
2000
- 2000-05-19 NZ NZ515580A patent/NZ515580A/en not_active IP Right Cessation
- 2000-05-19 DE DE60005507T patent/DE60005507T2/de not_active Expired - Lifetime
- 2000-05-19 IL IL14647100A patent/IL146471A0/xx active IP Right Grant
- 2000-05-19 CN CNB008080658A patent/CN1183153C/zh not_active Expired - Fee Related
- 2000-05-19 KR KR10-2001-7015044A patent/KR100537032B1/ko not_active Expired - Fee Related
- 2000-05-19 EP EP00932688A patent/EP1181302B1/de not_active Expired - Lifetime
- 2000-05-19 WO PCT/US2000/014036 patent/WO2000071558A1/en not_active Ceased
- 2000-05-19 MX MXPA01012038A patent/MXPA01012038A/es active IP Right Grant
- 2000-05-19 BR BR0010882-0A patent/BR0010882A/pt not_active Application Discontinuation
- 2000-05-19 AT AT00932688T patent/ATE250621T1/de not_active IP Right Cessation
- 2000-05-19 JP JP2001511301A patent/JP2003520776A/ja active Pending
- 2000-05-19 CA CA002375040A patent/CA2375040C/en not_active Expired - Fee Related
- 2000-05-19 ES ES00932688T patent/ES2206238T3/es not_active Expired - Lifetime
- 2000-05-19 AU AU50376/00A patent/AU760658B2/en not_active Ceased
- 2000-05-24 AR ARP000102555A patent/AR035909A1/es active IP Right Grant
- 2000-07-14 TW TW089110048A patent/TW593330B/zh not_active IP Right Cessation
2001
- 2001-11-13 IL IL146471A patent/IL146471A/en not_active IP Right Cessation
- 2001-11-20 NO NO20015662A patent/NO320854B1/no not_active IP Right Cessation
- 2001-11-22 ZA ZA200109626A patent/ZA200109626B/en unknown
2006
- 2006-07-31 JP JP2006207713A patent/JP2006348040A/ja active Pending

Also Published As

Publication number	Publication date
KR100537032B1 (ko)	2005-12-16
AU760658B2 (en)	2003-05-22
ES2206238T3 (es)	2004-05-16
US20020091099A1 (en)	2002-07-11
NO20015662D0 (no)	2001-11-20
WO2000071558A1 (en)	2000-11-30
IL146471A0 (en)	2002-07-25
CN1390228A (zh)	2003-01-08
NZ515580A (en)	2004-06-25
ATE250621T1 (de)	2003-10-15
KR20020092777A (ko)	2002-12-12
US6576619B2 (en)	2003-06-10
EP1181302A1 (de)	2002-02-27
AU5037600A (en)	2000-12-12
AR035909A1 (es)	2004-07-28
BR0010882A (pt)	2002-06-11
EP1181302B1 (de)	2003-09-24
NO20015662L (no)	2002-01-23
CA2375040A1 (en)	2000-11-30
MXPA01012038A (es)	2002-05-06
IL146471A (en)	2007-06-03
CN1183153C (zh)	2005-01-05
TW593330B (en)	2004-06-21
DE60005507T2 (de)	2004-06-24
JP2003520776A (ja)	2003-07-08
CA2375040C (en)	2006-02-07
DE60005507D1 (de)	2003-10-30
JP2006348040A (ja)	2006-12-28
ZA200109626B (en)	2004-03-10

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