SK82695A3 - Purine derivatives - Google Patents

Purine derivatives Download PDF

Info

Publication number: SK82695A3
Authority: SK; Slovakia
Prior art keywords: compound; formula; thio; propyl; benzothiazolyl
Prior art date: 1992-12-23

Application number

SK826-95A

Other languages

English (en)

Slovak (sk)

Inventor

Jesper Lau

Lars J S Knutsen

Malcolm Sheardown

Anker Hansen

Original Assignee

Novo Nordisk As

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.)

1992-12-23

Filing date

1993-12-21

Publication date

1996-04-03

1993-12-21 Application filed by Novo Nordisk As filed Critical Novo Nordisk As

1996-04-03 Publication of SK82695A3 publication Critical patent/SK82695A3/sk

Links

229940083251 peripheral vasodilators purine derivative Drugs 0.000 title description 2
125000000561 purinyl group Chemical class N1=C(N=C2N=CNC2=C1)* 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 130
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 45
150000003839 salts Chemical class 0.000 claims abstract description 15
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims abstract description 13
125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims abstract description 8
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 7
229910052736 halogen Inorganic materials 0.000 claims abstract description 6
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 5
150000002367 halogens Chemical group 0.000 claims abstract description 5
229910052717 sulfur Inorganic materials 0.000 claims abstract description 4
125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims abstract description 3
229910052760 oxygen Inorganic materials 0.000 claims abstract description 3
239000001257 hydrogen Substances 0.000 claims abstract 17
150000002431 hydrogen Chemical class 0.000 claims abstract 12
-1 amino, hydroxy Chemical group 0.000 claims description 92
238000000034 method Methods 0.000 claims description 80
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 55
238000006243 chemical reaction Methods 0.000 claims description 44
239000002126 C01EB10 - Adenosine Substances 0.000 claims description 31
229960005305 adenosine Drugs 0.000 claims description 31
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 22
CBHOOMGKXCMKIR-UHFFFAOYSA-N azane;methanol Chemical compound N.OC CBHOOMGKXCMKIR-UHFFFAOYSA-N 0.000 claims description 17
208000026555 breast adenosis Diseases 0.000 claims description 14
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 11
239000000203 mixture Substances 0.000 claims description 11
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 10
DIKBFYAXUHHXCS-UHFFFAOYSA-N bromoform Chemical compound BrC(Br)Br DIKBFYAXUHHXCS-UHFFFAOYSA-N 0.000 claims description 10
229910000288 alkali metal carbonate Inorganic materials 0.000 claims description 9
150000008041 alkali metal carbonates Chemical class 0.000 claims description 9
239000003814 drug Substances 0.000 claims description 9
239000004480 active ingredient Substances 0.000 claims description 8
239000003795 chemical substances by application Substances 0.000 claims description 8
125000005207 tetraalkylammonium group Chemical group 0.000 claims description 8
150000001412 amines Chemical class 0.000 claims description 7
125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 7
RILZRCJGXSFXNE-UHFFFAOYSA-N 2-[4-(trifluoromethoxy)phenyl]ethanol Chemical compound OCCC1=CC=C(OC(F)(F)F)C=C1 RILZRCJGXSFXNE-UHFFFAOYSA-N 0.000 claims description 6
201000010099 disease Diseases 0.000 claims description 6
239000008194 pharmaceutical composition Substances 0.000 claims description 6
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 5
229950005228 bromoform Drugs 0.000 claims description 5
208000015114 central nervous system disease Diseases 0.000 claims description 5
IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 claims description 5
125000004122 cyclic group Chemical group 0.000 claims description 5
239000003937 drug carrier Substances 0.000 claims description 5
QHDRKFYEGYYIIK-UHFFFAOYSA-N isovaleronitrile Chemical compound CC(C)CC#N QHDRKFYEGYYIIK-UHFFFAOYSA-N 0.000 claims description 5
239000000825 pharmaceutical preparation Substances 0.000 claims description 5
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
230000008569 process Effects 0.000 claims description 5
238000002360 preparation method Methods 0.000 claims description 4
239000000126 substance Substances 0.000 claims description 4
YYDIRVSTALSEKY-AUFSPBJRSA-N (2r,3r,4s,5r)-2-[6-[[(2r)-1-(1,3-benzothiazol-2-ylsulfanyl)propan-2-yl]amino]-2-(ethylamino)purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound C12=NC(NCC)=NC(N[C@H](C)CSC=3SC4=CC=CC=C4N=3)=C2N=CN1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O YYDIRVSTALSEKY-AUFSPBJRSA-N 0.000 claims description 3
BIIOFJUQTZOXNJ-SRNJXLPISA-N (2r,3r,4s,5r)-2-[6-[[(2r)-1-(1,3-benzothiazol-2-ylsulfanyl)propan-2-yl]amino]-2-bromopurin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound N([C@@H](CSC=1SC2=CC=CC=C2N=1)C)C(C=1N=C2)=NC(Br)=NC=1N2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O BIIOFJUQTZOXNJ-SRNJXLPISA-N 0.000 claims description 3
239000000460 chlorine Substances 0.000 claims description 3
125000001309 chloro group Chemical group Cl* 0.000 claims description 3
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
239000003085 diluting agent Substances 0.000 claims description 3
239000000758 substrate Substances 0.000 claims description 3
BIXYYZIIJIXVFW-UUOKFMHZSA-N (2R,3R,4S,5R)-2-(6-amino-2-chloro-9-purinyl)-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound C1=NC=2C(N)=NC(Cl)=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O BIXYYZIIJIXVFW-UUOKFMHZSA-N 0.000 claims description 2
FXGBAVYWSLHHDW-AUFSPBJRSA-N (2r,3r,4s,5r)-2-[6-[[(2r)-1-(1,3-benzothiazol-2-ylsulfanyl)propan-2-yl]amino]-2-(dimethylamino)purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound N([C@@H](CSC=1SC2=CC=CC=C2N=1)C)C(C=1N=C2)=NC(N(C)C)=NC=1N2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O FXGBAVYWSLHHDW-AUFSPBJRSA-N 0.000 claims description 2
229910005965 SO 2 Inorganic materials 0.000 claims description 2
229910052783 alkali metal Inorganic materials 0.000 claims description 2
125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
239000012351 deprotecting agent Substances 0.000 claims 8
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 5
QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 claims 4
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims 3
125000001589 carboacyl group Chemical group 0.000 claims 2
239000012038 nucleophile Substances 0.000 claims 2
229940127557 pharmaceutical product Drugs 0.000 claims 2
TYFCRQNDUUATPF-IYJBEEFKSA-N (2r,3r,4s,5r)-2-[6-[[(1s,2r)-2-(1,3-benzothiazol-2-ylsulfanyl)cyclohexyl]amino]-2-chloropurin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C2=NC(Cl)=NC(N[C@@H]3[C@@H](CCCC3)SC=3SC4=CC=CC=C4N=3)=C2N=C1 TYFCRQNDUUATPF-IYJBEEFKSA-N 0.000 claims 1
150000001340 alkali metals Chemical class 0.000 claims 1
210000000748 cardiovascular system Anatomy 0.000 claims 1
229910052801 chlorine Inorganic materials 0.000 claims 1
230000001351 cycling effect Effects 0.000 claims 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
238000009472 formulation Methods 0.000 claims 1
210000003169 central nervous system Anatomy 0.000 abstract description 9
230000002526 effect on cardiovascular system Effects 0.000 abstract description 3
125000000753 cycloalkyl group Chemical group 0.000 abstract description 2
125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 1
125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
125000000623 heterocyclic group Chemical group 0.000 abstract 1
RAHZWNYVWXNFOC-UHFFFAOYSA-N sulfur dioxide Inorganic materials O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 50
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 42
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 39
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 38
239000000243 solution Substances 0.000 description 32
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 31
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102000005962 receptors Human genes 0.000 description 27
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230000020176 deacylation Effects 0.000 description 19
238000005947 deacylation reaction Methods 0.000 description 19
235000019439 ethyl acetate Nutrition 0.000 description 17
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IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 15
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 12
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
239000011541 reaction mixture Substances 0.000 description 12
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
239000005557 antagonist Substances 0.000 description 10
230000000694 effects Effects 0.000 description 9
239000002253 acid Substances 0.000 description 8
IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 8
238000010511 deprotection reaction Methods 0.000 description 7
229940079593 drug Drugs 0.000 description 7
229920006395 saturated elastomer Polymers 0.000 description 7
YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 6
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 6
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YKCSWNJELCKJAC-BAYCTPFLSA-N (2r,3r,4s,5r)-2-[2-chloro-6-[[(2r)-1-(1,3-thiazol-2-ylsulfanyl)propan-2-yl]amino]purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound C([C@@H](C)NC=1C=2N=CN(C=2N=C(Cl)N=1)[C@H]1[C@@H]([C@H](O)[C@@H](CO)O1)O)SC1=NC=CS1 YKCSWNJELCKJAC-BAYCTPFLSA-N 0.000 description 3
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KDCGOANMDULRCW-UHFFFAOYSA-N Purine Natural products N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 3
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238000003818 flash chromatography Methods 0.000 description 3
239000008101 lactose Substances 0.000 description 3
GADIKQPUNWAMEB-UHFFFAOYSA-N methyl 4-ethyl-6,7-dimethoxy-9H-pyrido[5,4-b]indole-3-carboxylate Chemical compound N1C2=CC(OC)=C(OC)C=C2C2=C1C=NC(C(=O)OC)=C2CC GADIKQPUNWAMEB-UHFFFAOYSA-N 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
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Classifications

- 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
- 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
- A61K31/7056—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing five-membered rings with nitrogen as a 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
- 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
- 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
- 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
- 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

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

SK826-95A 1992-12-23 1993-12-21 Purine derivatives SK82695A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DK921552A DK155292D0 (da)	1992-12-23	1992-12-23	Kemiske forbindelser, deres fremstilling og anvendelse
PCT/DK1993/000434 WO1994014832A1 (en)	1992-12-23	1993-12-21	Purine derivatives

Publications (1)

Publication Number	Publication Date
SK82695A3 true SK82695A3 (en)	1996-04-03

Family

ID=8105999

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK826-95A SK82695A3 (en)	1992-12-23	1993-12-21	Purine derivatives

Country Status (18)

Country	Link
US (1)	US5484774A (bg)
EP (1)	EP0675896A1 (bg)
JP (1)	JPH08504777A (bg)
KR (1)	KR960700260A (bg)
AU (1)	AU690532B2 (bg)
BG (1)	BG61607B1 (bg)
CA (1)	CA2152341A1 (bg)
CZ (1)	CZ164295A3 (bg)
DK (1)	DK155292D0 (bg)
FI (1)	FI953127L (bg)
HU (1)	HUT72409A (bg)
IL (1)	IL108119A0 (bg)
NO (1)	NO952508L (bg)
NZ (1)	NZ259323A (bg)
PL (1)	PL175029B1 (bg)
SK (1)	SK82695A3 (bg)
WO (1)	WO1994014832A1 (bg)
ZA (1)	ZA939663B (bg)

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5683989A (en) *	1993-12-17	1997-11-04	Novo Nordisk A/S	Treatment of ischemias by administration of 2,N6 -substituted adenosines
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JP2001163854A (ja) *	1999-09-28	2001-06-19	Nippon Nohyaku Co Ltd	チオアルキルアミン誘導体及びその製造方法
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1992
- 1992-12-23 DK DK921552A patent/DK155292D0/da not_active Application Discontinuation
1993
- 1993-12-17 US US08/169,097 patent/US5484774A/en not_active Expired - Fee Related
- 1993-12-21 CZ CZ951642A patent/CZ164295A3/cs unknown
- 1993-12-21 PL PL93309610A patent/PL175029B1/pl unknown
- 1993-12-21 WO PCT/DK1993/000434 patent/WO1994014832A1/en not_active Application Discontinuation
- 1993-12-21 AU AU58093/94A patent/AU690532B2/en not_active Ceased
- 1993-12-21 KR KR1019950702609A patent/KR960700260A/ko not_active Application Discontinuation
- 1993-12-21 SK SK826-95A patent/SK82695A3/sk unknown
- 1993-12-21 JP JP6514703A patent/JPH08504777A/ja active Pending
- 1993-12-21 CA CA002152341A patent/CA2152341A1/en not_active Abandoned
- 1993-12-21 EP EP94903747A patent/EP0675896A1/en not_active Ceased
- 1993-12-21 IL IL10811993A patent/IL108119A0/xx unknown
- 1993-12-21 NZ NZ259323A patent/NZ259323A/en unknown
- 1993-12-21 HU HU9501856A patent/HUT72409A/hu unknown
- 1993-12-23 ZA ZA939663A patent/ZA939663B/xx unknown
1995
- 1995-06-22 BG BG99741A patent/BG61607B1/bg unknown
- 1995-06-22 FI FI953127A patent/FI953127L/fi not_active Application Discontinuation
- 1995-06-22 NO NO952508A patent/NO952508L/no unknown

Also Published As

Publication number	Publication date
BG61607B1 (bg)	1998-01-30
NZ259323A (en)	1996-06-25
IL108119A0 (en)	1994-04-12
FI953127L (fi)	1995-08-21
ZA939663B (en)	1995-06-23
CZ164295A3 (en)	1996-01-17
US5484774A (en)	1996-01-16
FI953127A0 (fi)	1995-06-22
WO1994014832A1 (en)	1994-07-07
EP0675896A1 (en)	1995-10-11
NO952508L (no)	1995-08-22
KR960700260A (ko)	1996-01-19
NO952508D0 (no)	1995-06-22
BG99741A (bg)	1996-04-30
AU690532B2 (en)	1998-04-30
DK155292D0 (da)	1992-12-23
JPH08504777A (ja)	1996-05-21
AU5809394A (en)	1994-07-19
CA2152341A1 (en)	1994-07-07
HU9501856D0 (en)	1995-08-28
HUT72409A (en)	1996-04-29
PL309610A1 (en)	1995-10-30
PL175029B1 (pl)	1998-10-30

Publication	Publication Date	Title
AU678053B2 (en)	1997-05-15	Chemical compounds, their preparation and use
SK82695A3 (en)	1996-04-03	Purine derivatives
US5578582A (en)	1996-11-26	Methods of treating ischemia with C2, N6 -disubstituted adenosine derivatives
US5430027A (en)	1995-07-04	2-chloro-N6 -substituted adenosines, their pharmaceutical compositions, and activity in treating ischemias
CZ20021223A3 (cs)	2003-05-14	Purinové deriváty
IL105673A (en)	1998-01-04	Use of n-substituted adenosine derivatives for the preparation of medicaments for treating myocardial or cerebral ischemia, certain novel n-substituted adenosine derivatives and pharmaceutical compositions containing them
US5683989A (en)	1997-11-04	Treatment of ischemias by administration of 2,N6 -substituted adenosines
WO1998016539A1 (en)	1998-04-23	Novel therapeutically active adenosine derivatives
US5672588A (en)	1997-09-30	Purine derivatives
JP3078579B2 (ja)	2000-08-21	ピリミジンヌクレオシド誘導体
Knutsen et al.	1995	C2, N 6-disubstituted adenosine derivatives
CN101010330A (zh)	2007-08-01	A1腺苷受体的部分和完全激动剂