BG61728B1 - 2,9-дизаместени пурин-6-они - Google Patents

2,9-дизаместени пурин-6-они Download PDF

Info

Publication number: BG61728B1
Authority: BG; Bulgaria
Prior art keywords: carbon atoms; straight; phenyl; substituted; branched chain
Prior art date: 1995-01-19

Application number

BG100292A

Other languages

Bulgarian (bg)

English (en)

Other versions

BG100292A (bg

Inventor

Ulrich Niewoehner

Erwin Bischoff

Helmuth Schuetz

Elisabeth Perzborn

Matthias Schramm

Original Assignee

Bayer Ag

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.)

1995-01-19

Filing date

1996-01-18

Publication date

1998-04-30

1996-01-18 Application filed by Bayer Ag filed Critical Bayer Ag

1996-07-31 Publication of BG100292A publication Critical patent/BG100292A/bg

1998-04-30 Publication of BG61728B1 publication Critical patent/BG61728B1/bg

Links

UYLWKSJTHLRFBX-UHFFFAOYSA-N purin-6-one Chemical class O=C1N=CN=C2N=CN=C12 UYLWKSJTHLRFBX-UHFFFAOYSA-N 0.000 title claims abstract description 15
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 7
230000000747 cardiac effect Effects 0.000 claims abstract 2
125000004432 carbon atom Chemical group C* 0.000 claims description 49
125000000217 alkyl group Chemical group 0.000 claims description 41
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 30
150000001875 compounds Chemical class 0.000 claims description 29
238000000034 method Methods 0.000 claims description 21
229910052739 hydrogen Inorganic materials 0.000 claims description 19
239000001257 hydrogen Substances 0.000 claims description 18
238000006243 chemical reaction Methods 0.000 claims description 14
125000003545 alkoxy group Chemical group 0.000 claims description 12
-1 bromo, carboxyl Chemical group 0.000 claims description 12
150000003839 salts Chemical class 0.000 claims description 12
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
125000001309 chloro group Chemical group Cl* 0.000 claims description 10
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
125000004093 cyano group Chemical group *C#N 0.000 claims description 9
239000003814 drug Substances 0.000 claims description 8
125000001153 fluoro group Chemical group F* 0.000 claims description 8
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
150000002431 hydrogen Chemical class 0.000 claims description 7
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 6
238000002360 preparation method Methods 0.000 claims description 6
239000012442 inert solvent Substances 0.000 claims description 5
208000001435 Thromboembolism Diseases 0.000 claims description 4
125000001246 bromo group Chemical group Br* 0.000 claims description 4
125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 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
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
229910052736 halogen Inorganic materials 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 4
208000027866 inflammatory disease Diseases 0.000 claims description 3
230000010933 acylation Effects 0.000 claims description 2
238000005917 acylation reaction Methods 0.000 claims description 2
150000001540 azides Chemical group 0.000 claims description 2
229910052799 carbon Inorganic materials 0.000 claims description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
125000000753 cycloalkyl group Chemical group 0.000 claims description 2
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 2
208000019622 heart disease Diseases 0.000 claims description 2
201000001881 impotence Diseases 0.000 claims description 2
230000003647 oxidation Effects 0.000 claims description 2
238000007254 oxidation reaction Methods 0.000 claims description 2
125000001424 substituent group Chemical group 0.000 claims description 2
238000006467 substitution reaction Methods 0.000 claims description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
125000004429 atom Chemical group 0.000 claims 1
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239000013543 active substance Substances 0.000 abstract description 3
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DEPDDPLQZYCHOH-UHFFFAOYSA-N 1h-imidazol-2-amine Chemical class NC1=NC=CN1 DEPDDPLQZYCHOH-UHFFFAOYSA-N 0.000 abstract 1
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239000002585 base Substances 0.000 description 7
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 7
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238000007363 ring formation reaction Methods 0.000 description 5
210000001519 tissue Anatomy 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
DVNYTAVYBRSTGK-UHFFFAOYSA-N 5-aminoimidazole-4-carboxamide Chemical class NC(=O)C=1N=CNC=1N DVNYTAVYBRSTGK-UHFFFAOYSA-N 0.000 description 4
QAXDVKBGZRMSHF-UHFFFAOYSA-N 6-acetyl-5-hydroxy-4-methoxy-7,8-dihydro-3h-pyrrolo[3,2-e]indole-2-carboxylic acid Chemical compound C1=2C=C(C(O)=O)NC=2C(OC)=C(O)C2=C1CCN2C(C)=O QAXDVKBGZRMSHF-UHFFFAOYSA-N 0.000 description 4
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PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 4
239000003960 organic solvent Substances 0.000 description 4
229910000027 potassium carbonate Inorganic materials 0.000 description 4
229910000104 sodium hydride Inorganic materials 0.000 description 4
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YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
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UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
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230000000694 effects Effects 0.000 description 3
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VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
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FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
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NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
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XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical group COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
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239000002270 dispersing agent Substances 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
239000008298 dragée Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000002526 effect on cardiovascular system Effects 0.000 description 1
239000003480 eluent Substances 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
210000003038 endothelium Anatomy 0.000 description 1
CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
CKFAFJGSVBYGIM-UHFFFAOYSA-N ethanol;2-methylpropan-2-ol Chemical compound CCO.CC(C)(C)O CKFAFJGSVBYGIM-UHFFFAOYSA-N 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
235000011087 fumaric acid Nutrition 0.000 description 1
229940052308 general anesthetics halogenated hydrocarbons Drugs 0.000 description 1
239000008187 granular material Substances 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
125000005842 heteroatom Chemical group 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
FDGQSTZJBFJUBT-UHFFFAOYSA-N hypoxanthine Chemical class O=C1NC=NC2=C1NC=N2 FDGQSTZJBFJUBT-UHFFFAOYSA-N 0.000 description 1
239000005457 ice water Substances 0.000 description 1
150000002460 imidazoles Chemical class 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
238000011534 incubation Methods 0.000 description 1
230000004054 inflammatory process Effects 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
201000004332 intermediate coronary syndrome Diseases 0.000 description 1
230000037041 intracellular level Effects 0.000 description 1
230000002262 irrigation Effects 0.000 description 1
238000003973 irrigation Methods 0.000 description 1
208000028867 ischemia Diseases 0.000 description 1
230000000302 ischemic effect Effects 0.000 description 1
KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
239000007788 liquid Substances 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
239000001630 malic acid Substances 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
230000004060 metabolic process Effects 0.000 description 1
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
238000002156 mixing Methods 0.000 description 1
208000010125 myocardial infarction Diseases 0.000 description 1
YZMHQCWXYHARLS-UHFFFAOYSA-N naphthalene-1,2-disulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(S(=O)(=O)O)=CC=C21 YZMHQCWXYHARLS-UHFFFAOYSA-N 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
239000002773 nucleotide Substances 0.000 description 1
125000003729 nucleotide group Chemical group 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
229940083251 peripheral vasodilators purine derivative Drugs 0.000 description 1
230000002085 persistent effect Effects 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000006187 pill Substances 0.000 description 1
230000008635 plant growth Effects 0.000 description 1
229920000117 poly(dioxanone) Polymers 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
230000002265 prevention Effects 0.000 description 1
210000002307 prostate Anatomy 0.000 description 1
238000000746 purification Methods 0.000 description 1
238000003127 radioimmunoassay Methods 0.000 description 1
230000000306 recurrent effect Effects 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
230000036303 septic shock Effects 0.000 description 1
208000017520 skin disease Diseases 0.000 description 1
210000000813 small intestine Anatomy 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000011973 solid acid Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
230000036262 stenosis Effects 0.000 description 1
208000037804 stenosis Diseases 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000003826 tablet Substances 0.000 description 1
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
230000002537 thrombolytic effect Effects 0.000 description 1
GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
DUAJIKVIRGATIW-UHFFFAOYSA-N trinitrogen(.) Chemical compound [N]=[N+]=[N-] DUAJIKVIRGATIW-UHFFFAOYSA-N 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
230000000304 vasodilatating effect Effects 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- 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
- C07D473/28—Oxygen atom
- C07D473/30—Oxygen atom attached in position 6, e.g. hypoxanthine
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
- 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

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Public Health (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Rheumatology (AREA)
Reproductive Health (AREA)
Diabetes (AREA)
Hematology (AREA)
Pain & Pain Management (AREA)
Heart & Thoracic Surgery (AREA)
Endocrinology (AREA)
Cardiology (AREA)
Urology & Nephrology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Saccharide Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

BG100292A 1995-01-19 1996-01-18 2,9-дизаместени пурин-6-они BG61728B1 (bg)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19501482A DE19501482A1 (de)	1995-01-19	1995-01-19	2,9-disubstituierte Purin-6-one

Publications (2)

Publication Number	Publication Date
BG100292A BG100292A (bg)	1996-07-31
BG61728B1 true BG61728B1 (bg)	1998-04-30

Family

ID=7751830

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BG100292A BG61728B1 (bg)	1995-01-19	1996-01-18	2,9-дизаместени пурин-6-они

Country Status (31)

Country	Link
US (1)	US5861404A (es)
EP (1)	EP0722944A1 (es)
JP (1)	JPH08231545A (es)
KR (1)	KR960029334A (es)
CN (1)	CN1135485A (es)
AR (1)	AR002953A1 (es)
AU (1)	AU4097996A (es)
BG (1)	BG61728B1 (es)
BR (1)	BR9600147A (es)
CA (1)	CA2167353A1 (es)
CO (1)	CO4700523A1 (es)
CZ (1)	CZ16696A3 (es)
DE (1)	DE19501482A1 (es)
EE (1)	EE9600018A (es)
FI (1)	FI960225L (es)
HR (1)	HRP960007A2 (es)
HU (1)	HUP9600106A3 (es)
IL (1)	IL116769A (es)
MA (1)	MA23778A1 (es)
NO (1)	NO960223L (es)
NZ (1)	NZ280830A (es)
PE (1)	PE64996A1 (es)
PL (1)	PL312354A1 (es)
SG (1)	SG50401A1 (es)
SK (1)	SK8096A3 (es)
SV (1)	SV1996000006A (es)
TN (2)	TNSN96007A1 (es)
TR (1)	TR199600028A2 (es)
TW (1)	TW314519B (es)
YU (1)	YU1396A (es)
ZA (1)	ZA96398B (es)

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DE19529102A1 (de) *	1995-08-08	1997-02-13	Kummer Horst Dieter	Verwendung von PDE-Inhibitoren bei der Behandlung von Harnblasenerkrankungen
US5824669A (en)	1996-03-22	1998-10-20	Nitromed, Inc.	Nitrosated and nitrosylated compounds and compositions and their use for treating respiratory disorders
USRE37234E1 (en)	1996-11-01	2001-06-19	Nitromed, Inc.	Nitrosated and nitrosylated phosphodiestrase inhibitor compounds, compositions and their uses
US5958926A (en)	1996-11-01	1999-09-28	Nitromed, Inc.	Nitrosated and nitrosylated phosphodiesterase inhibitor compounds, compositions and their uses
WO1999003858A1 (fr) *	1997-07-15	1999-01-28	Japan Energy Corporation	Derives purine et leur application medicinale
CA2309350C (en) *	1997-11-12	2007-04-03	Mitsubishi Chemical Corporation	Purine derivatives and medicaments comprising the same as active ingredient
USRE39112E1 (en) *	1998-01-05	2006-05-30	Eisai Co., Ltd.	Purine derivatives and adenosine A2 receptor antagonists serving as preventives/remedies for diabetes
US6124303A (en) *	1998-09-11	2000-09-26	Cell Pathways, Inc.	Method for inhibiting neoplastic cells and related conditions by exposure to 9-substituted 2-(2-N-aloxyphenyl) purin-6-ones
US6268372B1 (en)	1998-09-11	2001-07-31	Cell Pathways, Inc.	Method for inhibiting neoplastic cells and related conditions by exposure to 2,9-disubstituted purin-6-ones
US6660745B1 (en) *	1999-05-11	2003-12-09	Mitsubishi Chemical Corporation	Purine derivative dihydrate, drugs containing the same as the active ingredient and intermediate in the production thereof
GB9924020D0 (en)	1999-10-11	1999-12-15	Pfizer Ltd	Pharmaceutically active compounds
ATE552013T1 (de) *	2000-09-06	2012-04-15	Mitsubishi Tanabe Pharma Corp	Zubereitungen zur oralen anwendung
KR100750554B1 (ko) *	2001-02-15	2007-08-20	다나베 세이야꾸 가부시키가이샤	구강 내 속붕괴성 정제
US6479493B1 (en)	2001-08-23	2002-11-12	Cell Pathways, Inc.	Methods for treatment of type I diabetes
US7893101B2 (en)	2002-03-20	2011-02-22	Celgene Corporation	Solid forms comprising (+)-2-[1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-4-acetylaminoisoindoline-1,3-dione, compositions thereof, and uses thereof
US7276529B2 (en)	2002-03-20	2007-10-02	Celgene Corporation	Methods of the treatment or prevention of exercise-induced asthma using (+)-2-[1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-4-acetylaminoisoindoline-1,3-dione
US7208516B2 (en)	2002-03-20	2007-04-24	Celgene Corporation	Methods of the treatment of psoriatic arthritis using (+)-2-[1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-4-acetylaminoisoindoline-1,3-dione
US6962940B2 (en)	2002-03-20	2005-11-08	Celgene Corporation	(+)-2-[1-(3-Ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-4-acetylaminoisoindoline-1,3-dione: methods of using and compositions thereof
CN102742513A (zh) *	2012-07-17	2012-10-24	南京熊猫机电制造有限公司	一种喂食栏装置
US10300042B2 (en)	2014-06-23	2019-05-28	Celgene Corporation	Apremilast for the treatment of a liver disease or a liver function abnormality
US11198699B2 (en)	2019-04-02	2021-12-14	Aligos Therapeutics, Inc.	Compounds targeting PRMT5
JP7385467B2 (ja) *	2019-12-26	2023-11-22	キッセイ薬品工業株式会社	ヒポキサンチン化合物

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4451478A (en) *	1982-03-12	1984-05-29	Newport Pharmaceuticals International, Inc.	Imidazole compounds
IL76546A (en) *	1984-10-12	1988-12-30	Warner Lambert Co	9-(heteroarylalkyl)-6-purine(thi)one derivatives,their preparation and pharmaceutical compositions containing them
GB9213623D0 (en) *	1992-06-26	1992-08-12	Pfizer Ltd	Therapeutic agents

1995
- 1995-01-19 DE DE19501482A patent/DE19501482A1/de not_active Withdrawn
- 1995-12-27 TW TW084113907A patent/TW314519B/zh active
1996
- 1996-01-08 EP EP96100156A patent/EP0722944A1/de not_active Withdrawn
- 1996-01-08 HR HR19501482.0A patent/HRP960007A2/hr not_active Application Discontinuation
- 1996-01-12 US US08/587,321 patent/US5861404A/en not_active Expired - Fee Related
- 1996-01-12 YU YU1396A patent/YU1396A/sh unknown
- 1996-01-15 TR TR96/00028A patent/TR199600028A2/xx unknown
- 1996-01-15 AU AU40979/96A patent/AU4097996A/en not_active Abandoned
- 1996-01-16 NZ NZ280830A patent/NZ280830A/en unknown
- 1996-01-16 CA CA002167353A patent/CA2167353A1/en not_active Abandoned
- 1996-01-16 IL IL11676996A patent/IL116769A/en not_active IP Right Cessation
- 1996-01-17 SG SG1996000260A patent/SG50401A1/en unknown
- 1996-01-17 FI FI960225A patent/FI960225L/fi unknown
- 1996-01-17 TN TNTNSN96007A patent/TNSN96007A1/fr unknown
- 1996-01-17 PL PL96312354A patent/PL312354A1/xx unknown
- 1996-01-17 TN TNTNSN96006A patent/TNSN96006A1/fr unknown
- 1996-01-18 ZA ZA96398A patent/ZA96398B/xx unknown
- 1996-01-18 JP JP8023473A patent/JPH08231545A/ja active Pending
- 1996-01-18 CZ CZ96166A patent/CZ16696A3/cs unknown
- 1996-01-18 BR BR9600147A patent/BR9600147A/pt active Search and Examination
- 1996-01-18 NO NO960223A patent/NO960223L/no unknown
- 1996-01-18 HU HU9600106A patent/HUP9600106A3/hu unknown
- 1996-01-18 BG BG100292A patent/BG61728B1/bg unknown
- 1996-01-18 EE EE9600018A patent/EE9600018A/xx unknown
- 1996-01-18 KR KR1019960001002A patent/KR960029334A/ko not_active Application Discontinuation
- 1996-01-18 SK SK80-96A patent/SK8096A3/sk unknown
- 1996-01-18 MA MA24133A patent/MA23778A1/fr unknown
- 1996-01-19 PE PE1996000043A patent/PE64996A1/es not_active Application Discontinuation
- 1996-01-19 CN CN96101917A patent/CN1135485A/zh active Pending
- 1996-01-19 CO CO96002169A patent/CO4700523A1/es unknown
- 1996-01-19 SV SV1996000006A patent/SV1996000006A/es unknown
- 1996-01-19 AR ARP960101088A patent/AR002953A1/es unknown

Also Published As

Publication number	Publication date
HUP9600106A2 (en)	1997-05-28
AU4097996A (en)	1996-07-25
CZ16696A3 (en)	1996-08-14
YU1396A (sh)	1999-03-04
HRP960007A2 (en)	1998-02-28
CN1135485A (zh)	1996-11-13
US5861404A (en)	1999-01-19
SK8096A3 (en)	1996-08-07
PL312354A1 (en)	1996-07-22
NZ280830A (en)	1998-04-27
ZA96398B (en)	1996-08-28
EP0722944A1 (de)	1996-07-24
TW314519B (es)	1997-09-01
CO4700523A1 (es)	1998-12-29
AR002953A1 (es)	1998-05-27
EE9600018A (et)	1996-08-15
FI960225L (fi)	1996-07-20
IL116769A (en)	1998-12-06
TR199600028A2 (tr)	1996-08-21
SG50401A1 (en)	1998-07-20
KR960029334A (ko)	1996-08-17
BR9600147A (pt)	1998-01-06
SV1996000006A (es)	1996-10-29
TNSN96006A1 (fr)	2005-03-15
JPH08231545A (ja)	1996-09-10
CA2167353A1 (en)	1996-07-20
HU9600106D0 (en)	1996-03-28
DE19501482A1 (de)	1996-07-25
MA23778A1 (fr)	1996-10-01
FI960225A0 (fi)	1996-01-17
IL116769A0 (en)	1996-05-14
BG100292A (bg)	1996-07-31
TNSN96007A1 (fr)	2005-03-15
NO960223L (no)	1996-07-22
HUP9600106A3 (en)	1998-04-28
PE64996A1 (es)	1997-03-09
NO960223D0 (no)	1996-01-18

Publication	Publication Date	Title
BG61728B1 (bg)	1998-04-30	2,9-дизаместени пурин-6-они
AU704102B2 (en)	1999-04-15	2,8-disubstituted quinazolinones
KR101491938B1 (ko)	2015-02-10	Ｉｐ 수용체 효능제 헤테로시클릭 화합물
AU727615B2 (en)	2000-12-14	1,5-dihydro-pyrazolo(3,4-d)-pyrimidinone derivatives
AU720305B2 (en)	2000-05-25	Purin-6-one derivatives
EP2802589B1 (en)	2016-01-06	Fused pyrroles as ip receptor agonists for the treatment of pulmonary arterial hypertension (pah) and related disorders
CZ374992A3 (en)	1993-10-13	Polycyclic guanine derivatives
WO2013105063A1 (en)	2013-07-18	Fused piperidines as ip receptor agonists for the treatment of pulmonary arterial hypertension (pah) and related disorders
NZ336124A (en)	2001-03-30	5-aralkyl or (aryl, heteroaryl or heteroarylalkyl) substituted pyrrolo[3,4-d]pyrimidinone derivatives and medicaments
KR20090106633A (ko)	2009-10-09	ＰＤＥ5 억제제로서 유용한 6-벤질-2,3,4,7-테트라히드로-인돌로[2,3-ｃ]퀴놀린 화합물
BG61729B1 (bg)	1998-04-30	9-заместени-2-(2-норм-алкоксифенил)пурин-6-они
EP0183848B1 (en)	1990-09-12	Polyazaheterocyclic derivatives, process for their preparation, and pharmaceutical composition
EP4029858A1 (en)	2022-07-20	Pyrimidine compound and preparation method therefor
US20080108652A1 (en)	2008-05-08	Imidazo (4,5-B) pyridine-derivatives as inducible no-synthase inhibitors
JPH04221384A (ja)	1992-08-11	選択的アデノシン受容体アゴニスト及びアンタゴニスト
WO1993017023A1 (fr)	1993-09-02	Derives de pyrazolopyrimidines antagonistes des recepteurs a l'angiotensine ii
US6458792B1 (en)	2002-10-01	Compounds
US6949652B2 (en)	2005-09-27	Crystalline forms of 3-isopropyl-6-[4-(2,5-difluoro-phenyl)-oxazol-5-yl]-[1,2,4]triazolo-[4,3-A]pyridine
EP2885297B1 (fr)	2017-10-11	Pyrido[3,2-d]pyrimidines trisubstituées, leurs procédés de préparation et leurs utilisations en thérapeutique
KR20030065519A (ko)	2003-08-06	신규 피리딘 치환 피라졸로피리딘 유도체
WO2009037302A1 (en)	2009-03-26	5-substituted-1, 4-benz0diazepines as phosphodiesterase inhibitors
JPH11269071A (ja)	1999-10-05	糸球体疾患の予防及び治療剤