SK3192003A3 - Xanthine phosphodiesterase V inhibitors, process for their preparation, pharmaceutical composition comprising same and their use - Google Patents

Xanthine phosphodiesterase V inhibitors, process for their preparation, pharmaceutical composition comprising same and their use Download PDF

Info

Publication number: SK3192003A3
Authority: SK; Slovakia
Prior art keywords: substituents; alkyl; pharmaceutical composition; group; aryl
Prior art date: 2000-09-19

Application number

SK319-2003A

Other languages

English (en)

Slovak (sk)

Inventor

Samuel Chackalamannil

Yuguang Wang

Craig D Boyle

Andrew W Stamford

Original Assignee

Schering Corp

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.)

2000-09-19

Filing date

2001-09-17

Publication date

2003-08-05

2001-09-17 Application filed by Schering Corp filed Critical Schering Corp

2003-08-05 Publication of SK3192003A3 publication Critical patent/SK3192003A3/sk

Links

LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical compound O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 title claims abstract description 107
239000002590 phosphodiesterase V inhibitor Substances 0.000 title claims abstract description 60
229940075420 xanthine Drugs 0.000 title claims abstract description 52
239000008194 pharmaceutical composition Substances 0.000 title claims description 60
238000000034 method Methods 0.000 title claims description 12
238000002360 preparation method Methods 0.000 title claims description 11
230000008569 process Effects 0.000 title claims description 4
150000001875 compounds Chemical class 0.000 claims abstract description 187
125000001424 substituent group Chemical group 0.000 claims abstract description 119
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 47
125000000592 heterocycloalkyl group Chemical group 0.000 claims abstract description 26
125000000392 cycloalkenyl group Chemical group 0.000 claims abstract description 15
125000006647 (C3-C15) cycloalkyl group Chemical group 0.000 claims abstract description 9
125000000217 alkyl group Chemical group 0.000 claims description 107
125000003118 aryl group Chemical group 0.000 claims description 77
-1 hydrocarbon radical Chemical class 0.000 claims description 56
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 48
229940082638 cardiac stimulant phosphodiesterase inhibitors Drugs 0.000 claims description 43
125000001072 heteroaryl group Chemical group 0.000 claims description 43
239000002571 phosphodiesterase inhibitor Substances 0.000 claims description 43
VHVGFEDTMPYCSX-UHFFFAOYSA-N [1-[[2,2-dimethyl-3-[[4-(oxoazaniumylmethylidene)pyridin-1-yl]methoxy]propoxy]methyl]pyridin-4-ylidene]methyl-oxoazanium;dichloride Chemical compound [Cl-].[Cl-].C1=CC(=C[NH+]=O)C=CN1COCC(C)(C)COCN1C=CC(=C[NH+]=O)C=C1 VHVGFEDTMPYCSX-UHFFFAOYSA-N 0.000 claims description 39
201000001881 impotence Diseases 0.000 claims description 38
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 37
238000011282 treatment Methods 0.000 claims description 37
229910052739 hydrogen Inorganic materials 0.000 claims description 33
208000010228 Erectile Dysfunction Diseases 0.000 claims description 31
239000001257 hydrogen Substances 0.000 claims description 31
125000004432 carbon atom Chemical group C* 0.000 claims description 29
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 27
201000010099 disease Diseases 0.000 claims description 25
125000000623 heterocyclic group Chemical group 0.000 claims description 25
125000000753 cycloalkyl group Chemical group 0.000 claims description 24
125000003710 aryl alkyl group Chemical group 0.000 claims description 23
125000003342 alkenyl group Chemical group 0.000 claims description 22
208000035475 disorder Diseases 0.000 claims description 21
208000024891 symptom Diseases 0.000 claims description 19
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 18
125000000304 alkynyl group Chemical group 0.000 claims description 17
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
239000003814 drug Substances 0.000 claims description 16
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 15
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 14
CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 14
125000005842 heteroatom Chemical group 0.000 claims description 13
229910002651 NO3 Inorganic materials 0.000 claims description 12
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 12
125000003545 alkoxy group Chemical group 0.000 claims description 12
125000002837 carbocyclic group Chemical group 0.000 claims description 12
229910052736 halogen Inorganic materials 0.000 claims description 12
150000002367 halogens Chemical class 0.000 claims description 12
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 11
125000005843 halogen group Chemical group 0.000 claims description 11
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
125000004103 aminoalkyl group Chemical group 0.000 claims description 10
125000004181 carboxyalkyl group Chemical group 0.000 claims description 10
125000004663 dialkyl amino group Chemical group 0.000 claims description 10
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 10
239000003112 inhibitor Substances 0.000 claims description 10
125000002877 alkyl aryl group Chemical group 0.000 claims description 8
150000002148 esters Chemical class 0.000 claims description 8
125000003282 alkyl amino group Chemical group 0.000 claims description 7
229910052799 carbon Inorganic materials 0.000 claims description 7
125000001188 haloalkyl group Chemical group 0.000 claims description 7
125000005646 oximino group Chemical group 0.000 claims description 7
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 6
239000004215 Carbon black (E152) Substances 0.000 claims description 6
150000001350 alkyl halides Chemical class 0.000 claims description 6
125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 6
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
125000004093 cyano group Chemical group *C#N 0.000 claims description 6
238000006264 debenzylation reaction Methods 0.000 claims description 6
230000002526 effect on cardiovascular system Effects 0.000 claims description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
229930195733 hydrocarbon Natural products 0.000 claims description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
125000004001 thioalkyl group Chemical group 0.000 claims description 6
206010020772 Hypertension Diseases 0.000 claims description 5
125000002252 acyl group Chemical group 0.000 claims description 5
230000029936 alkylation Effects 0.000 claims description 5
238000005804 alkylation reaction Methods 0.000 claims description 5
150000001412 amines Chemical class 0.000 claims description 5
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 5
206010012601 diabetes mellitus Diseases 0.000 claims description 5
125000004952 trihaloalkoxy group Chemical group 0.000 claims description 5
125000004385 trihaloalkyl group Chemical group 0.000 claims description 5
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
ZOOGRGPOEVQQDX-UUOKFMHZSA-N 3',5'-cyclic GMP Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=C(NC2=O)N)=C2N=C1 ZOOGRGPOEVQQDX-UUOKFMHZSA-N 0.000 claims description 4
GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 4
229910019142 PO4 Inorganic materials 0.000 claims description 4
239000002253 acid Substances 0.000 claims description 4
239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 4
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 4
230000005595 deprotonation Effects 0.000 claims description 4
238000010537 deprotonation reaction Methods 0.000 claims description 4
230000007935 neutral effect Effects 0.000 claims description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 4
239000010452 phosphate Substances 0.000 claims description 4
125000000547 substituted alkyl group Chemical group 0.000 claims description 4
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 3
206010002383 Angina Pectoris Diseases 0.000 claims description 3
206010003645 Atopy Diseases 0.000 claims description 3
208000023275 Autoimmune disease Diseases 0.000 claims description 3
208000010412 Glaucoma Diseases 0.000 claims description 3
208000022461 Glomerular disease Diseases 0.000 claims description 3
208000031773 Insulin resistance syndrome Diseases 0.000 claims description 3
206010028980 Neoplasm Diseases 0.000 claims description 3
206010036049 Polycystic ovaries Diseases 0.000 claims description 3
208000001647 Renal Insufficiency Diseases 0.000 claims description 3
208000025609 Urogenital disease Diseases 0.000 claims description 3
125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 3
125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 3
125000004414 alkyl thio group Chemical group 0.000 claims description 3
238000002399 angioplasty Methods 0.000 claims description 3
239000002333 angiotensin II receptor antagonist Substances 0.000 claims description 3
239000005557 antagonist Substances 0.000 claims description 3
125000002102 aryl alkyloxo group Chemical group 0.000 claims description 3
125000004391 aryl sulfonyl group Chemical group 0.000 claims description 3
201000011510 cancer Diseases 0.000 claims description 3
125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 3
239000003136 dopamine receptor stimulating agent Substances 0.000 claims description 3
125000004185 ester group Chemical group 0.000 claims description 3
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 3
231100000852 glomerular disease Toxicity 0.000 claims description 3
125000005114 heteroarylalkoxy group Chemical group 0.000 claims description 3
125000004446 heteroarylalkyl group Chemical group 0.000 claims description 3
201000001421 hyperglycemia Diseases 0.000 claims description 3
201000006370 kidney failure Diseases 0.000 claims description 3
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 3
208000031225 myocardial ischemia Diseases 0.000 claims description 3
201000008383 nephritis Diseases 0.000 claims description 3
125000005010 perfluoroalkyl group Chemical group 0.000 claims description 3
201000010065 polycystic ovary syndrome Diseases 0.000 claims description 3
208000002815 pulmonary hypertension Diseases 0.000 claims description 3
208000037803 restenosis Diseases 0.000 claims description 3
125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 3
125000004665 trialkylsilyl group Chemical group 0.000 claims description 3
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims description 2
125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
239000005541 ACE inhibitor Substances 0.000 claims description 2
206010006895 Cachexia Diseases 0.000 claims description 2
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WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 2
102000004257 Potassium Channel Human genes 0.000 claims description 2
102000011016 Type 5 Cyclic Nucleotide Phosphodiesterases Human genes 0.000 claims description 2
108010037581 Type 5 Cyclic Nucleotide Phosphodiesterases Proteins 0.000 claims description 2
102000004305 alpha Adrenergic Receptors Human genes 0.000 claims description 2
108090000861 alpha Adrenergic Receptors Proteins 0.000 claims description 2
229940044094 angiotensin-converting-enzyme inhibitor Drugs 0.000 claims description 2
239000002308 endothelin receptor antagonist Substances 0.000 claims description 2
239000008103 glucose Substances 0.000 claims description 2
230000002140 halogenating effect Effects 0.000 claims description 2
230000026030 halogenation Effects 0.000 claims description 2
238000005658 halogenation reaction Methods 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims description 2
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
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239000000336 melanocortin receptor agonist Substances 0.000 claims description 2
239000003757 phosphotransferase inhibitor Substances 0.000 claims description 2
108020001213 potassium channel Proteins 0.000 claims description 2
125000004171 alkoxy aryl group Chemical group 0.000 claims 3
125000005027 hydroxyaryl group Chemical group 0.000 claims 3
125000004390 alkyl sulfonyl group Chemical group 0.000 claims 2
238000004519 manufacturing process Methods 0.000 claims 2
101710129690 Angiotensin-converting enzyme inhibitor Proteins 0.000 claims 1
101710086378 Bradykinin-potentiating and C-type natriuretic peptides Proteins 0.000 claims 1
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230000007815 allergy Effects 0.000 claims 1
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238000003780 insertion Methods 0.000 claims 1
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239000002243 precursor Substances 0.000 claims 1
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206010057671 Female sexual dysfunction Diseases 0.000 abstract description 6
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XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 60
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YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
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IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 22
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SJSNUMAYCRRIOM-QFIPXVFZSA-N valsartan Chemical compound C1=CC(CN(C(=O)CCCC)[C@@H](C(C)C)C(O)=O)=CC=C1C1=CC=CC=C1C1=NN=N[N]1 SJSNUMAYCRRIOM-QFIPXVFZSA-N 0.000 description 1
229960002381 vardenafil Drugs 0.000 description 1
235000010493 xanthan gum Nutrition 0.000 description 1
239000000230 xanthan gum Substances 0.000 description 1
229940082509 xanthan gum Drugs 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/04—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61P13/00—Drugs for disorders of the urinary system
- 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
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
- 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
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/10—Drugs for genital or sexual disorders; Contraceptives for impotence
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/06—Antiglaucoma agents or miotics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
- 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
- A61P9/10—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
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/04—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms
- C07D473/06—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/04—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms
- C07D473/06—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3
- C07D473/08—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3 with methyl radicals in positions 1 and 3, e.g. theophylline

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Transplantation (AREA)
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Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

SK319-2003A 2000-09-19 2001-09-17 Xanthine phosphodiesterase V inhibitors, process for their preparation, pharmaceutical composition comprising same and their use SK3192003A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US23356700P	2000-09-19	2000-09-19
PCT/US2001/028983 WO2002024698A1 (en)	2000-09-19	2001-09-17	Xanthine phosphodiesterase v inhibitors

Publications (1)

Publication Number	Publication Date
SK3192003A3 true SK3192003A3 (en)	2003-08-05

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SK319-2003A SK3192003A3 (en)	2000-09-19	2001-09-17	Xanthine phosphodiesterase V inhibitors, process for their preparation, pharmaceutical composition comprising same and their use

Country Status (29)

Country	Link
US (6)	US6821978B2 (zh)
EP (1)	EP1319003B1 (zh)
JP (2)	JP4015547B2 (zh)
KR (1)	KR100610417B1 (zh)
CN (1)	CN1252071C (zh)
AR (1)	AR035199A1 (zh)
AT (1)	ATE433451T1 (zh)
AU (2)	AU2001291022B2 (zh)
BR (1)	BR0113953A (zh)
CA (1)	CA2421910C (zh)
CY (1)	CY1109329T1 (zh)
DE (1)	DE60138955D1 (zh)
DK (1)	DK1319003T3 (zh)
EC (1)	ECSP034519A (zh)
ES (1)	ES2326956T3 (zh)
HU (1)	HUP0303016A3 (zh)
IL (1)	IL154839A0 (zh)
MX (1)	MXPA03002361A (zh)
NO (1)	NO328753B1 (zh)
NZ (1)	NZ524433A (zh)
PE (1)	PE20020469A1 (zh)
PL (1)	PL205188B1 (zh)
PT (1)	PT1319003E (zh)
RU (1)	RU2302420C9 (zh)
SI (1)	SI1319003T1 (zh)
SK (1)	SK3192003A3 (zh)
TW (1)	TWI241301B (zh)
WO (1)	WO2002024698A1 (zh)
ZA (1)	ZA200301863B (zh)

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2001
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- 2001-09-17 MX MXPA03002361A patent/MXPA03002361A/es active IP Right Grant
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- 2001-09-17 KR KR1020037003898A patent/KR100610417B1/ko not_active Expired - Fee Related
- 2001-09-17 BR BR0113953-3A patent/BR0113953A/pt not_active Application Discontinuation
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- 2001-09-18 PE PE2001000936A patent/PE20020469A1/es not_active Application Discontinuation
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2003
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2004
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Also Published As

Publication number	Publication date
US7531544B2 (en)	2009-05-12
EP1319003A1 (en)	2003-06-18
WO2002024698A1 (en)	2002-03-28
PE20020469A1 (es)	2002-06-18
KR100610417B1 (ko)	2006-08-08
JP2007297409A (ja)	2007-11-15
HUP0303016A3 (en)	2007-03-28
PL361729A1 (en)	2004-10-04
RU2302420C2 (ru)	2007-07-10
US20080058354A1 (en)	2008-03-06
NO328753B1 (no)	2010-05-03
US6821978B2 (en)	2004-11-23
AU9102201A (en)	2002-04-02
AR035199A1 (es)	2004-05-05
US20050075349A1 (en)	2005-04-07
KR20030036800A (ko)	2003-05-09
EP1319003B1 (en)	2009-06-10
NO20031238L (no)	2003-05-14
HK1056550A1 (zh)	2004-02-20
CN1252071C (zh)	2006-04-19
US7268141B2 (en)	2007-09-11
AU2001291022B2 (en)	2007-01-18
US20040229885A1 (en)	2004-11-18
ZA200301863B (en)	2004-06-22
ES2326956T3 (es)	2009-10-22
CY1109329T1 (el)	2014-07-02
DE60138955D1 (en)	2009-07-23
US20040167137A1 (en)	2004-08-26
ECSP034519A (es)	2003-04-25
JP2004509892A (ja)	2004-04-02
CA2421910C (en)	2007-07-10
BR0113953A (pt)	2003-07-22
CN1460105A (zh)	2003-12-03
NO20031238D0 (no)	2003-03-18
DK1319003T3 (da)	2009-09-28
SI1319003T1 (sl)	2009-10-31
ATE433451T1 (de)	2009-06-15
PL205188B1 (pl)	2010-03-31
IL154839A0 (en)	2003-10-31
JP4015547B2 (ja)	2007-11-28
TWI241301B (en)	2005-10-11
US20020169174A1 (en)	2002-11-14
RU2302420C9 (ru)	2008-12-10
CA2421910A1 (en)	2002-03-28
HUP0303016A2 (hu)	2003-12-29
MXPA03002361A (es)	2003-06-30
PT1319003E (pt)	2009-07-23
US20050182077A1 (en)	2005-08-18
NZ524433A (en)	2004-09-24

Publication	Publication Date	Title
SK3192003A3 (en)	2003-08-05	Xanthine phosphodiesterase V inhibitors, process for their preparation, pharmaceutical composition comprising same and their use
AU2001291022A1 (en)	2002-06-20	Xanthine phosphodiesterase v inhibitors
EP1421084B1 (en)	2008-05-14	Polycyclic guanine phosphodiesterase v inhibitors
JP3447292B2 (ja)	2003-09-16	イミダゾピリジン及び胃腸の疾病の治療のためのその使用
AU2009331179A1 (en)	2011-08-11	Novel bicyclic heterocyclic compound
CA2465893A1 (en)	2003-05-22	Polycyclic guanine derivative phosphodiesterase v inhibitors
CA2141366A1 (en)	1995-08-02	Treatment of heart rhythm disorders by administration of 3-phenylsulfonyl-3,7-diazabicyclo[3.3.1]nonane compounds
HK1056550B (zh)	2009-08-14	黃嘌呤磷酸二酯酶v抑制劑
EP1790652A1 (en)	2007-05-30	Polycyclic guanine phosphodiesterase V inhibitors
HK1064668B (zh)	2008-12-24	多環鳥嘌呤磷酸二酯酶v抑制劑
JPH04128285A (ja)	1992-04-28	キサンチン誘導体
JPH03218378A (ja)	1991-09-25	キサンチン誘導体

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2012-05-03	FB9A	Suspension of patent application procedure