IL93893A - History of imidazo-) A-2,1 (purine and imidazo) C-1,2 (pyridazo) E -4,3 (pyramidine transformed in the fall, selectivity for adenosine receptor and raw preparations - Google Patents

History of imidazo-) A-2,1 (purine and imidazo) C-1,2 (pyridazo) E -4,3 (pyramidine transformed in the fall, selectivity for adenosine receptor and raw preparations

Info

Publication number: IL93893A
Authority: IL; Israel
Prior art keywords: phenyl; hydrogen; dihydro; compound according; adenosine
Prior art date: 1989-03-29

Application number

IL9389390A

Other languages

English (en)

Hebrew (he)

Other versions

IL93893A0 (en

Original Assignee

Merrell Pharma 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.)

1989-03-29

Filing date

1990-03-26

Publication date

1994-07-31

1990-03-26 Application filed by Merrell Pharma Inc filed Critical Merrell Pharma Inc

1990-12-23 Publication of IL93893A0 publication Critical patent/IL93893A0/xx

1994-07-31 Publication of IL93893A publication Critical patent/IL93893A/en

Links

239000008194 pharmaceutical composition Substances 0.000 title claims description 6
108050000203 Adenosine receptors Proteins 0.000 title abstract description 44
102000009346 Adenosine receptors Human genes 0.000 title abstract description 44
KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 title description 6
229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 title description 2
150000003230 pyrimidines Chemical class 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 72
239000001257 hydrogen Substances 0.000 claims abstract description 42
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 42
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 30
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 29
150000002431 hydrogen Chemical group 0.000 claims abstract description 29
125000000217 alkyl group Chemical group 0.000 claims abstract description 16
HMFHBZSHGGEWLO-TXICZTDVSA-N beta-D-ribose Chemical group OC[C@H]1O[C@@H](O)[C@H](O)[C@@H]1O HMFHBZSHGGEWLO-TXICZTDVSA-N 0.000 claims abstract description 12
125000003545 alkoxy group Chemical group 0.000 claims abstract description 11
230000036772 blood pressure Effects 0.000 claims abstract description 9
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 7
230000003247 decreasing effect Effects 0.000 claims abstract description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 6
-1 β- -ribofuranosyl Chemical group 0.000 claims description 21
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 16
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 15
239000004480 active ingredient Substances 0.000 claims 2
FKJPSWPVFWKSSA-MRXNPFEDSA-N (4R)-4-benzyl-10-phenyl-3,6,8,10,11-pentazatricyclo[7.3.0.02,6]dodeca-1(9),2,7,11-tetraene Chemical compound C([C@H](N=C12)CC=3C=CC=CC=3)N1C=NC1=C2C=NN1C1=CC=CC=C1 FKJPSWPVFWKSSA-MRXNPFEDSA-N 0.000 claims 1
230000027455 binding Effects 0.000 abstract description 17
150000003838 adenosines Chemical class 0.000 abstract description 15
230000000694 effects Effects 0.000 abstract description 14
230000001766 physiological effect Effects 0.000 abstract description 10
238000001727 in vivo Methods 0.000 abstract description 8
238000000338 in vitro Methods 0.000 abstract description 6
239000000296 purinergic P1 receptor antagonist Substances 0.000 abstract description 4
239000000825 pharmaceutical preparation Substances 0.000 abstract description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 100
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 description 61
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 54
VAJVDSVGBWFCLW-UHFFFAOYSA-N 3-Phenyl-1-propanol Chemical compound OCCCC1=CC=CC=C1 VAJVDSVGBWFCLW-UHFFFAOYSA-N 0.000 description 48
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 48
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 47
239000000047 product Substances 0.000 description 43
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 40
238000006243 chemical reaction Methods 0.000 description 35
239000002904 solvent Substances 0.000 description 31
239000002126 C01EB10 - Adenosine Substances 0.000 description 29
229960005305 adenosine Drugs 0.000 description 29
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 28
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
238000010992 reflux Methods 0.000 description 26
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 22
238000003818 flash chromatography Methods 0.000 description 21
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 20
102100025358 Probable G-protein coupled receptor 162 Human genes 0.000 description 19
239000012528 membrane Substances 0.000 description 19
102000005962 receptors Human genes 0.000 description 18
108020003175 receptors Proteins 0.000 description 18
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XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
229960004592 isopropanol Drugs 0.000 description 16
238000003756 stirring Methods 0.000 description 16
235000019441 ethanol Nutrition 0.000 description 15
ZUBZATZOEPUUQF-UHFFFAOYSA-N isopropylhexane Natural products CCCCCCC(C)C ZUBZATZOEPUUQF-UHFFFAOYSA-N 0.000 description 15
239000003921 oil Substances 0.000 description 13
239000002244 precipitate Substances 0.000 description 13
238000012360 testing method Methods 0.000 description 13
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
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230000008484 agonism Effects 0.000 description 12
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VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
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QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 6
239000000556 agonist Substances 0.000 description 6
230000008485 antagonism Effects 0.000 description 6
239000000284 extract Substances 0.000 description 6
125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 6
239000011734 sodium Substances 0.000 description 6
229910052708 sodium Inorganic materials 0.000 description 6
239000007858 starting material Substances 0.000 description 6
STVVMTBJNDTZBF-SECBINFHSA-N (2r)-2-amino-3-phenylpropan-1-ol Chemical compound OC[C@H](N)CC1=CC=CC=C1 STVVMTBJNDTZBF-SECBINFHSA-N 0.000 description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
STVVMTBJNDTZBF-VIFPVBQESA-N L-phenylalaninol Chemical compound OC[C@@H](N)CC1=CC=CC=C1 STVVMTBJNDTZBF-VIFPVBQESA-N 0.000 description 5
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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 description 4
PUARFAPITOZVIH-UHFFFAOYSA-N 2,6-dichloro-9-phenylpurine Chemical compound C12=NC(Cl)=NC(Cl)=C2N=CN1C1=CC=CC=C1 PUARFAPITOZVIH-UHFFFAOYSA-N 0.000 description 4
HRRVLSKRYVIEPR-UHFFFAOYSA-N 6-hydroxy-5-nitroso-1H-pyrimidine-2,4-dione Chemical compound OC1=NC(O)=C(N=O)C(O)=N1 HRRVLSKRYVIEPR-UHFFFAOYSA-N 0.000 description 4
IFKGLNGMNJBJSN-UHFFFAOYSA-N 9-phenyl-8-sulfanylidene-3,7-dihydropurine-2,6-dione Chemical compound S=C1NC=2C(=O)NC(=O)NC=2N1C1=CC=CC=C1 IFKGLNGMNJBJSN-UHFFFAOYSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
XKMLYUALXHKNFT-UUOKFMHZSA-N Guanosine-5'-triphosphate Chemical compound C1=2NC(N)=NC(=O)C=2N=CN1[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O XKMLYUALXHKNFT-UUOKFMHZSA-N 0.000 description 4
241001465754 Metazoa Species 0.000 description 4
241000700159 Rattus Species 0.000 description 4
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
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RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 4
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239000012362 glacial acetic acid Substances 0.000 description 4
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235000011167 hydrochloric acid Nutrition 0.000 description 4
238000011534 incubation Methods 0.000 description 4
229910052943 magnesium sulfate Inorganic materials 0.000 description 4
230000001404 mediated effect Effects 0.000 description 4
239000012044 organic layer Substances 0.000 description 4
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229940094443 oxytocics prostaglandins Drugs 0.000 description 4
239000008188 pellet Substances 0.000 description 4
QKFJKGMPGYROCL-UHFFFAOYSA-N phenyl isothiocyanate Chemical compound S=C=NC1=CC=CC=C1 QKFJKGMPGYROCL-UHFFFAOYSA-N 0.000 description 4
150000003180 prostaglandins Chemical class 0.000 description 4
230000002685 pulmonary effect Effects 0.000 description 4
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FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
229940086542 triethylamine Drugs 0.000 description 4
RIRGCFBBHQEQQH-SSFGXONLSA-N (-)-n6-(2-phenylisopropyl)adenosine Chemical compound C([C@@H](C)NC=1C=2N=CN(C=2N=CN=1)[C@H]1[C@@H]([C@H](O)[C@@H](CO)O1)O)C1=CC=CC=C1 RIRGCFBBHQEQQH-SSFGXONLSA-N 0.000 description 3
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UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical compound C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 description 1
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Classifications

- 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
- C07D487/12—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 three hetero rings
- C07D487/14—Ortho-condensed systems
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
- 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
- A61P25/20—Hypnotics; Sedatives
- 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
- A61P25/24—Antidepressants
- 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
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
- A61P39/02—Antidotes
- 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
- A61P9/08—Vasodilators for multiple indications
- 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
- 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
- A61P9/12—Antihypertensives
- 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
- C07D473/34—Nitrogen atom attached in position 6, e.g. adenine
- 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

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Neurosurgery (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Psychiatry (AREA)
Pain & Pain Management (AREA)
Vascular Medicine (AREA)
Urology & Nephrology (AREA)
Toxicology (AREA)
Anesthesiology (AREA)
Pulmonology (AREA)
Biochemistry (AREA)
Biotechnology (AREA)
Genetics & Genomics (AREA)
Molecular Biology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Saccharide Compounds (AREA)

IL9389390A 1989-03-29 1990-03-26 History of imidazo-) A-2,1 (purine and imidazo) C-1,2 (pyridazo) E -4,3 (pyramidine transformed in the fall, selectivity for adenosine receptor and raw preparations IL93893A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US33040089A	1989-03-29	1989-03-29

Publications (2)

Publication Number	Publication Date
IL93893A0 IL93893A0 (en)	1990-12-23
IL93893A true IL93893A (en)	1994-07-31

Family

ID=23289598

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL9389390A IL93893A (en)	1989-03-29	1990-03-26	History of imidazo-) A-2,1 (purine and imidazo) C-1,2 (pyridazo) E -4,3 (pyramidine transformed in the fall, selectivity for adenosine receptor and raw preparations

Country Status (18)

Country	Link
EP (1)	EP0390111B1 (de)
JP (1)	JP3014000B2 (de)
KR (1)	KR0150635B1 (de)
CN (1)	CN1029972C (de)
AR (1)	AR245720A1 (de)
AT (1)	ATE111466T1 (de)
AU (1)	AU623755B2 (de)
CA (1)	CA2013381C (de)
DE (1)	DE69012388T2 (de)
ES (1)	ES2063851T3 (de)
FI (1)	FI95133C (de)
HU (1)	HU203349B (de)
IE (1)	IE63545B1 (de)
IL (1)	IL93893A (de)
NO (1)	NO173997C (de)
NZ (1)	NZ233077A (de)
PT (1)	PT93589B (de)
ZA (1)	ZA902282B (de)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA2028235C (en) *	1989-10-20	1997-01-21	Fumio Suzuki	Condensed purine derivatives
NZ238609A (en) *	1990-06-21	1993-12-23	Schering Corp	Polycyclic guanine derivatives; preparation, pharmaceutical compositions,
DE19629378A1 (de) *	1996-07-20	1998-01-29	Boehringer Ingelheim Kg	Neue Triazolopurine, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel
DE60018216T2 (de)	1999-12-24	2006-02-16	Kyowa Hakko Kogyo Co., Ltd.	Kondensierte purinderivate

1990
- 1990-03-23 AU AU52182/90A patent/AU623755B2/en not_active Ceased
- 1990-03-23 ZA ZA902282A patent/ZA902282B/xx unknown
- 1990-03-26 NZ NZ233077A patent/NZ233077A/xx unknown
- 1990-03-26 IL IL9389390A patent/IL93893A/en not_active IP Right Cessation
- 1990-03-27 HU HU901857A patent/HU203349B/hu not_active IP Right Cessation
- 1990-03-28 IE IE114290A patent/IE63545B1/en not_active IP Right Cessation
- 1990-03-28 DE DE69012388T patent/DE69012388T2/de not_active Expired - Fee Related
- 1990-03-28 ES ES90105919T patent/ES2063851T3/es not_active Expired - Lifetime
- 1990-03-28 PT PT93589A patent/PT93589B/pt not_active IP Right Cessation
- 1990-03-28 FI FI901550A patent/FI95133C/fi not_active IP Right Cessation
- 1990-03-28 CN CN90101709A patent/CN1029972C/zh not_active Expired - Fee Related
- 1990-03-28 EP EP90105919A patent/EP0390111B1/de not_active Expired - Lifetime
- 1990-03-28 NO NO901424A patent/NO173997C/no not_active IP Right Cessation
- 1990-03-28 AR AR90316475A patent/AR245720A1/es active
- 1990-03-28 AT AT90105919T patent/ATE111466T1/de not_active IP Right Cessation
- 1990-03-28 KR KR1019900004160A patent/KR0150635B1/ko not_active Expired - Fee Related
- 1990-03-29 CA CA002013381A patent/CA2013381C/en not_active Expired - Fee Related
- 1990-03-29 JP JP2079071A patent/JP3014000B2/ja not_active Expired - Fee Related

Also Published As

Publication number	Publication date
CN1029972C (zh)	1995-10-11
IE901142L (en)	1990-09-29
DE69012388D1 (de)	1994-10-20
HU901857D0 (en)	1990-08-28
FI95133B (fi)	1995-09-15
NO901424D0 (no)	1990-03-28
ES2063851T3 (es)	1995-01-16
EP0390111A3 (de)	1991-05-08
EP0390111A2 (de)	1990-10-03
FI901550A0 (fi)	1990-03-28
NZ233077A (en)	1992-12-23
JP3014000B2 (ja)	2000-02-28
PT93589A (pt)	1990-11-20
ATE111466T1 (de)	1994-09-15
AR245720A1 (es)	1994-02-28
AU5218290A (en)	1990-10-04
CN1045974A (zh)	1990-10-10
KR0150635B1 (ko)	1998-10-15
IE63545B1 (en)	1995-05-17
NO901424L (no)	1990-10-01
PT93589B (pt)	1996-06-28
JPH02289574A (ja)	1990-11-29
HU203349B (en)	1991-07-29
CA2013381A1 (en)	1990-09-29
ZA902282B (en)	1990-12-28
IL93893A0 (en)	1990-12-23
HUT54160A (en)	1991-01-28
KR900014390A (ko)	1990-10-23
NO173997C (no)	1994-03-02
DE69012388T2 (de)	1995-04-27
EP0390111B1 (de)	1994-09-14
AU623755B2 (en)	1992-05-21
FI95133C (fi)	1995-12-27
NO173997B (no)	1993-11-22
CA2013381C (en)	2000-06-20

Legal Events

Date

Code

Title

Description

1996-03-31

KB

Patent renewed

2005-07-25

MM9K

Patent not in force due to non-payment of renewal fees

2006-09-05

HC

Change of name of proprietor(s)

Owner name: AVENTIS INC.

Free format text: FORMER NAME:MERRELL PHARMACEUTICALS INC.

Publication	Publication Date	Title
US8273750B2 (en)	2012-09-25	Organic compounds
EP0390112B1 (de)	1998-01-28	Selektive Adenosinrezeptor-Liganden
US5329007A (en)	1994-07-12	Selective adenosine receptor agents
AU632914B2 (en)	1993-01-14	Selective adenosine receptor agents
US5064947A (en)	1991-11-12	Selective adenosine reseptor compounds
EP0390111B1 (de)	1994-09-14	Selektive Adenosinrezeptor-Verbindungen
US5086176A (en)	1992-02-04	Tricyclic fused adenine derivatives
EP0662975B1 (de)	1997-03-26	2-substituierte adenosine mit a-2 rezeptor affinität
US5391739A (en)	1995-02-21	Selective adenosine receptor agents
EP0884318A1 (de)	1998-12-16	Kondensierte purinderivate
AU676323B2 (en)	1997-03-06	8-substituted xanthines as selective adenosine receptor agents
US5426101A (en)	1995-06-20	2-substituted adenosines with A-2 receptor affinity