SK391891A3 - Xanthine derivatives and pharmaceutical composition comprising same - Google Patents

Xanthine derivatives and pharmaceutical composition comprising same Download PDF

Info

Publication number: SK391891A3
Authority: SK; Slovakia
Prior art keywords: formula; dicyclopropylmethyl; group; compound; xanthine derivatives
Prior art date: 1989-03-23

Application number

SK3918-91A

Other languages

English (en)

Slovak (sk)

Inventor

Harald Maschler

Barbara Ann Spicer

Harry Smith

Original Assignee

Beecham Wuelfing Gmbh And Co K

Beecham Group Plc

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.)

1989-03-23

Filing date

1991-12-19

Publication date

2000-12-11

1991-12-19 Application filed by Beecham Wuelfing Gmbh And Co K, Beecham Group Plc filed Critical Beecham Wuelfing Gmbh And Co K

2000-12-11 Publication of SK391891A3 publication Critical patent/SK391891A3/sk

Links

LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical class O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 title claims description 20
229940083747 low-ceiling diuretics xanthine derivative Drugs 0.000 title claims description 12
239000008194 pharmaceutical composition Substances 0.000 title claims description 5
150000003839 salts Chemical class 0.000 claims abstract description 26
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 18
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 11
125000000217 alkyl group Chemical group 0.000 claims abstract description 8
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 8
125000004448 alkyl carbonyl group Chemical group 0.000 claims abstract description 7
239000001257 hydrogen Substances 0.000 claims abstract description 7
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 5
208000026106 cerebrovascular disease Diseases 0.000 claims abstract description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 3
125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract 2
-1 1,3-Dicyclohexylmethyl-8-aminoxanthine 1,3-dicyclopropyl-8-aminoxanthine Chemical compound 0.000 claims description 17
239000004480 active ingredient Substances 0.000 claims description 12
201000010099 disease Diseases 0.000 claims description 7
125000004432 carbon atom Chemical group C* 0.000 claims description 6
125000003277 amino group Chemical group 0.000 claims description 5
KXZCOUISCHFBJW-UHFFFAOYSA-N 1,3-bis(cyclopropylmethyl)-8-nitro-7h-purine-2,6-dione Chemical compound O=C1N(CC2CC2)C(=O)C=2NC([N+](=O)[O-])=NC=2N1CC1CC1 KXZCOUISCHFBJW-UHFFFAOYSA-N 0.000 claims description 4
208000018262 Peripheral vascular disease Diseases 0.000 claims description 4
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
239000003937 drug carrier Substances 0.000 claims description 4
LYNPMBCGTLJEDK-UHFFFAOYSA-N 1,3-dicyclohexyl-8-nitro-7h-purine-2,6-dione Chemical compound O=C1N(C2CCCCC2)C(=O)C=2NC([N+](=O)[O-])=NC=2N1C1CCCCC1 LYNPMBCGTLJEDK-UHFFFAOYSA-N 0.000 claims description 3
CCCFLROKQFJCMT-UHFFFAOYSA-N 8-bromo-1,3-bis(cyclohexylmethyl)-7h-purine-2,6-dione Chemical compound O=C1N(CC2CCCCC2)C(=O)C=2NC(Br)=NC=2N1CC1CCCCC1 CCCFLROKQFJCMT-UHFFFAOYSA-N 0.000 claims description 3
FOGDEWDBZWEMOH-UHFFFAOYSA-N 8-chloro-1,3-dicyclohexyl-7h-purine-2,6-dione Chemical compound O=C1N(C2CCCCC2)C(=O)C=2NC(Cl)=NC=2N1C1CCCCC1 FOGDEWDBZWEMOH-UHFFFAOYSA-N 0.000 claims description 3
208000026935 allergic disease Diseases 0.000 claims description 3
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
YWIDXLMXWUIXOJ-UHFFFAOYSA-N 1,3-bis(cyclohexylmethyl)-8-nitro-7h-purine-2,6-dione Chemical compound O=C1N(CC2CCCCC2)C(=O)C=2NC([N+](=O)[O-])=NC=2N1CC1CCCCC1 YWIDXLMXWUIXOJ-UHFFFAOYSA-N 0.000 claims description 2
DAHOPKGGXGFYEW-UHFFFAOYSA-N 1,3-bis(cyclohexylmethyl)-8-piperidin-1-yl-7h-purine-2,6-dione Chemical compound C1=2N=C(N3CCCCC3)NC=2C(=O)N(CC2CCCCC2)C(=O)N1CC1CCCCC1 DAHOPKGGXGFYEW-UHFFFAOYSA-N 0.000 claims description 2
INEZLVVKMUWARI-UHFFFAOYSA-N 1,3-bis(cyclopropylmethyl)-8-morpholin-4-yl-7h-purine-2,6-dione Chemical compound C1=2N=C(N3CCOCC3)NC=2C(=O)N(CC2CC2)C(=O)N1CC1CC1 INEZLVVKMUWARI-UHFFFAOYSA-N 0.000 claims description 2
QZMLAWVVWTZRLF-UHFFFAOYSA-N 8-chloro-1,3-bis(cyclopropylmethyl)-7h-purine-2,6-dione Chemical compound O=C1N(CC2CC2)C(=O)C=2NC(Cl)=NC=2N1CC1CC1 QZMLAWVVWTZRLF-UHFFFAOYSA-N 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
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
125000002757 morpholinyl group Chemical group 0.000 claims description 2
125000003386 piperidinyl group Chemical group 0.000 claims description 2
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 2
FBWOCBWJZRIJBU-UHFFFAOYSA-N 1,3-bis(cyclobutylmethyl)-8-nitro-7h-purine-2,6-dione Chemical compound O=C1N(CC2CCC2)C(=O)C=2NC([N+](=O)[O-])=NC=2N1CC1CCC1 FBWOCBWJZRIJBU-UHFFFAOYSA-N 0.000 claims 1
LZNXLJQGCRQYDT-UHFFFAOYSA-N 1,3-bis(cyclopentylmethyl)-8-nitro-7h-purine-2,6-dione Chemical compound O=C1N(CC2CCCC2)C(=O)C=2NC([N+](=O)[O-])=NC=2N1CC1CCCC1 LZNXLJQGCRQYDT-UHFFFAOYSA-N 0.000 claims 1
UFAQFYMNIFOKGO-UHFFFAOYSA-N 1,3-bis(cyclopropylmethyl)-8-piperidin-1-yl-7h-purine-2,6-dione Chemical compound C1=2N=C(N3CCCCC3)NC=2C(=O)N(CC2CC2)C(=O)N1CC1CC1 UFAQFYMNIFOKGO-UHFFFAOYSA-N 0.000 claims 1
AGCQOIRZOOICOR-UHFFFAOYSA-N 1,3-bis(cyclopropylmethyl)-8-pyrrolidin-1-yl-7h-purine-2,6-dione Chemical compound C1=2N=C(N3CCCC3)NC=2C(=O)N(CC2CC2)C(=O)N1CC1CC1 AGCQOIRZOOICOR-UHFFFAOYSA-N 0.000 claims 1
WQBKKJIJEGGRNX-UHFFFAOYSA-N 8-amino-1,3-bis(cyclobutylmethyl)-7h-purine-2,6-dione Chemical compound O=C1N(CC2CCC2)C(=O)C=2NC(N)=NC=2N1CC1CCC1 WQBKKJIJEGGRNX-UHFFFAOYSA-N 0.000 claims 1
MVILGRWJMAJOGO-UHFFFAOYSA-N 8-amino-1,3-bis(cyclopentylmethyl)-7h-purine-2,6-dione Chemical compound O=C1N(CC2CCCC2)C(=O)C=2NC(N)=NC=2N1CC1CCCC1 MVILGRWJMAJOGO-UHFFFAOYSA-N 0.000 claims 1
KSPYMJJKQMWWNB-UHFFFAOYSA-N cipamfylline Chemical compound O=C1N(CC2CC2)C(=O)C=2NC(N)=NC=2N1CC1CC1 KSPYMJJKQMWWNB-UHFFFAOYSA-N 0.000 claims 1
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125000000623 heterocyclic group Chemical group 0.000 abstract description 2
231100000252 nontoxic Toxicity 0.000 abstract 1
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238000002360 preparation method Methods 0.000 description 30
238000005481 NMR spectroscopy Methods 0.000 description 27
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 26
239000000047 product Substances 0.000 description 25
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
238000006243 chemical reaction Methods 0.000 description 21
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
239000007787 solid Substances 0.000 description 18
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
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
238000002844 melting Methods 0.000 description 12
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QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
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238000003756 stirring Methods 0.000 description 9
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PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
238000009472 formulation Methods 0.000 description 8
229920005654 Sephadex Polymers 0.000 description 7
239000012507 Sephadex™ Substances 0.000 description 7
239000003795 chemical substances by application Substances 0.000 description 7
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 description 7
238000012360 testing method Methods 0.000 description 7
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
239000002585 base Substances 0.000 description 6
210000004369 blood Anatomy 0.000 description 6
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XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 6
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DHXHKBLFJYJGKP-UHFFFAOYSA-N 1,1-bis(cyclohexylmethyl)urea Chemical compound C1CCCCC1CN(C(=O)N)CC1CCCCC1 DHXHKBLFJYJGKP-UHFFFAOYSA-N 0.000 description 3
PEUMRAZSOJOADF-UHFFFAOYSA-N 1,3-dibutyl-8-nitro-7h-purine-2,6-dione Chemical compound O=C1N(CCCC)C(=O)N(CCCC)C2=C1NC([N+]([O-])=O)=N2 PEUMRAZSOJOADF-UHFFFAOYSA-N 0.000 description 3
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 3
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239000004317 sodium nitrate Substances 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
238000000527 sonication Methods 0.000 description 1
239000001593 sorbitan monooleate Substances 0.000 description 1
235000011069 sorbitan monooleate Nutrition 0.000 description 1
229940035049 sorbitan monooleate Drugs 0.000 description 1
238000012453 sprague-dawley rat model Methods 0.000 description 1
206010041823 squamous cell carcinoma Diseases 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
150000003431 steroids Chemical class 0.000 description 1
239000000021 stimulant Substances 0.000 description 1
150000003890 succinate salts Chemical class 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
238000001356 surgical procedure Methods 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
150000003892 tartrate salts Chemical class 0.000 description 1
229960000278 theophylline Drugs 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
239000008009 topical excipient Substances 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
230000002792 vascular Effects 0.000 description 1
239000008215 water for injection Substances 0.000 description 1
238000005303 weighing Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
- A61K31/52—Purines, e.g. adenine
- 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
- 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
- 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- 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
- 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
- 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

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Heart & Thoracic Surgery (AREA)
Biomedical Technology (AREA)
Cardiology (AREA)
Neurosurgery (AREA)
Neurology (AREA)
Pulmonology (AREA)
Vascular Medicine (AREA)
Immunology (AREA)
Urology & Nephrology (AREA)
Hospice & Palliative Care (AREA)
Psychiatry (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Saccharide Compounds (AREA)
Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

SK3918-91A 1989-03-23 1991-12-19 Xanthine derivatives and pharmaceutical composition comprising same SK391891A3 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB898906792A GB8906792D0 (en)	1989-03-23	1989-03-23	Treatment and compounds

Publications (1)

Publication Number	Publication Date
SK391891A3 true SK391891A3 (en)	2000-12-11

Family

ID=10653940

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK3918-91A SK391891A3 (en)	1989-03-23	1991-12-19	Xanthine derivatives and pharmaceutical composition comprising same

Country Status (27)

Country	Link
US (4)	US5981535A (fr)
EP (2)	EP0389282B1 (fr)
JP (1)	JP2510889B2 (fr)
KR (1)	KR0160768B1 (fr)
CN (1)	CN1031641C (fr)
AT (1)	ATE213498T1 (fr)
AU (1)	AU629315B2 (fr)
CA (1)	CA2012686C (fr)
CZ (1)	CZ391891A3 (fr)
DE (1)	DE69033915T2 (fr)
DK (1)	DK0389282T3 (fr)
ES (1)	ES2173074T3 (fr)
FI (1)	FI95033C (fr)
GB (1)	GB8906792D0 (fr)
HK (1)	HK1040392A1 (fr)
HU (1)	HU207081B (fr)
IL (1)	IL93832A (fr)
MA (1)	MA21800A1 (fr)
MY (1)	MY109737A (fr)
NO (1)	NO175592C (fr)
NZ (1)	NZ233021A (fr)
PL (1)	PL164811B1 (fr)
PT (1)	PT93527B (fr)
SA (1)	SA90100215B1 (fr)
SK (1)	SK391891A3 (fr)
ZA (1)	ZA902170B (fr)
ZW (1)	ZW3690A1 (fr)

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CH654008A5 (fr) *	1979-05-22	1986-01-31	Nestle Sa	Procede de preparation de 1,3,7-trialkylxanthines.
IT1200944B (it) *	1982-08-10	1989-01-27	Malesci Sas	Derivati xantinici,procedimento per la loro preparazione,composizione farmaceutiche che il contengono e loro impiego terapeutico
US4593095A (en) *	1983-02-18	1986-06-03	The Johns Hopkins University	Xanthine derivatives
US4567183A (en) *	1983-03-11	1986-01-28	Analgesic Associates	Analgesic and anti-inflammatory compositions comprising xanthines and methods of using same
US4558051A (en) *	1983-10-11	1985-12-10	Richardson-Vicks, Inc.	Analgesic and anti-inflammatory compositions comprising xanthines and methods of using same
DE3406533A1 (de) *	1984-02-23	1985-08-29	Boehringer Mannheim Gmbh, 6800 Mannheim	Verwendung von adenosin-derivaten als antiallergica und arzneimittel, die diese enthalten
US4666914A (en) *	1985-05-13	1987-05-19	Schering Corporation	Anti-inflammatory and anti-allergic substituted-2,3-dihydro-6-(hydroxy)pyrimido[2,1-f]-purine-4,8(1H,9H)-diones
GB8610136D0 (en) *	1986-04-25	1986-05-29	Wellcome Found	Compounds
GB8621869D0 (en) *	1986-09-11	1986-10-15	Beecham Group Plc	Treatment
KR890005052A (ko)	1986-12-22	1989-05-11	기오르지오 스키니나	신규 피페리딘 유도체
IT1197516B (it) *	1986-12-24	1988-11-30	Abc Ist Biolog Chem Spa	Derivati teofillinmetilanici e teofillinmetilditianici procedimento per la loro preparazione e composizioni farmaceutiche che li comprendono

1989
- 1989-03-23 GB GB898906792A patent/GB8906792D0/en active Pending
1990
- 1990-03-20 MA MA22044A patent/MA21800A1/fr unknown
- 1990-03-21 IL IL9383290A patent/IL93832A/en unknown
- 1990-03-21 AU AU52083/90A patent/AU629315B2/en not_active Ceased
- 1990-03-21 PT PT93527A patent/PT93527B/pt not_active IP Right Cessation
- 1990-03-21 NZ NZ233021A patent/NZ233021A/en unknown
- 1990-03-21 NO NO901300A patent/NO175592C/no unknown
- 1990-03-21 ZA ZA902170A patent/ZA902170B/xx unknown
- 1990-03-21 CA CA002012686A patent/CA2012686C/fr not_active Expired - Fee Related
- 1990-03-22 DE DE69033915T patent/DE69033915T2/de not_active Expired - Fee Related
- 1990-03-22 ES ES90303093T patent/ES2173074T3/es not_active Expired - Lifetime
- 1990-03-22 FI FI901447A patent/FI95033C/fi not_active IP Right Cessation
- 1990-03-22 EP EP90303093A patent/EP0389282B1/fr not_active Expired - Lifetime
- 1990-03-22 HU HU901792A patent/HU207081B/hu not_active IP Right Cessation
- 1990-03-22 AT AT90303093T patent/ATE213498T1/de not_active IP Right Cessation
- 1990-03-22 ZW ZW36/90A patent/ZW3690A1/xx unknown
- 1990-03-22 DK DK90303093T patent/DK0389282T3/da active
- 1990-03-22 EP EP00203905A patent/EP1120417A3/fr not_active Withdrawn
- 1990-03-22 KR KR1019900003902A patent/KR0160768B1/ko not_active IP Right Cessation
- 1990-03-23 PL PL90284429A patent/PL164811B1/pl not_active IP Right Cessation
- 1990-03-23 JP JP2075359A patent/JP2510889B2/ja not_active Expired - Fee Related
- 1990-03-23 CN CN90102240A patent/CN1031641C/zh not_active Expired - Fee Related
- 1990-03-23 MY MYPI90000465A patent/MY109737A/en unknown
- 1990-05-08 SA SA90100215A patent/SA90100215B1/ar unknown
1991
- 1991-12-19 SK SK3918-91A patent/SK391891A3/sk unknown
- 1991-12-19 CZ CS913918A patent/CZ391891A3/cs unknown
1995
- 1995-06-07 US US08/474,093 patent/US5981535A/en not_active Expired - Fee Related
- 1995-06-07 US US08/477,157 patent/US5734051A/en not_active Expired - Fee Related
1998
- 1998-02-17 US US09/024,252 patent/US6180791B1/en not_active Expired - Fee Related
- 1998-12-15 HK HK02100617.1A patent/HK1040392A1/zh unknown
2000
- 2000-11-08 US US09/708,338 patent/US6531600B1/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
CZ391891A3 (en)	1993-11-17
KR0160768B1 (ko)	1998-12-01
HU901792D0 (en)	1990-06-28
FI95033C (fi)	1995-12-11
ES2173074T3 (es)	2002-10-16
JP2510889B2 (ja)	1996-06-26
NO175592B (no)	1994-07-25
KR900013962A (ko)	1990-10-22
DK0389282T3 (da)	2002-06-03
NO901300D0 (no)	1990-03-21
US6180791B1 (en)	2001-01-30
NZ233021A (en)	1993-12-23
IL93832A (en)	1994-07-31
US5981535A (en)	1999-11-09
HU207081B (en)	1993-03-01
CA2012686A1 (fr)	1990-09-23
GB8906792D0 (en)	1989-05-10
EP0389282A3 (fr)	1992-07-01
SA90100215B1 (ar)	2001-10-07
ATE213498T1 (de)	2002-03-15
JPH02273676A (ja)	1990-11-08
FI95033B (fi)	1995-08-31
EP1120417A2 (fr)	2001-08-01
DE69033915D1 (de)	2002-03-28
HUT54155A (en)	1991-01-28
NO901300L (no)	1990-09-24
AU5208390A (en)	1990-09-27
HK1040392A1 (zh)	2002-06-07
MY109737A (en)	1997-05-31
EP1120417A3 (fr)	2001-08-08
NO175592C (no)	1994-11-02
CN1047502A (zh)	1990-12-05
EP0389282B1 (fr)	2002-02-20
DE69033915T2 (de)	2002-10-10
MA21800A1 (fr)	1990-12-31
ZA902170B (en)	1991-03-27
US5734051A (en)	1998-03-31
PT93527B (pt)	1996-08-30
CN1031641C (zh)	1996-04-24
US6531600B1 (en)	2003-03-11
IL93832A0 (en)	1990-12-23
PT93527A (pt)	1990-11-07
ZW3690A1 (en)	1991-02-06
AU629315B2 (en)	1992-10-01
PL164811B1 (pl)	1994-10-31
CA2012686C (fr)	1999-12-07
FI901447A0 (fi)	1990-03-22
EP0389282A2 (fr)	1990-09-26

Publication	Publication Date	Title
SK391891A3 (en)	2000-12-11	Xanthine derivatives and pharmaceutical composition comprising same
US4294831A (en)	1981-10-13	Purine derivatives
US4199574A (en)	1980-04-22	Methods and compositions for treating viral infections and guanine acyclic nucleosides
DE69419755T2 (de)	2000-02-17	Chemische verbindungen mit pde-iv inhibitierende wirkung
DE69132291T2 (de)	2000-12-14	Xanthinderivate
JPH09501918A (ja)	1997-02-25	酸化窒素合成酵素活性を有するアミジン誘導体
PL158285B1 (en)	1992-08-31	Method of obtaining novel derivatives of 9-(2-hydroxyetoxymethyl-guanine
EP0369744B1 (fr)	1994-09-21	Dérivés de Xanthine, procédé pour leur préparation et compositions pharmaceutiques les contenant
JPS63297381A (ja)	1988-12-05	９−〔２−（ヒドロキシメチル）シクロアルキルメチル〕グアニン類
KR940010033B1 (ko)	1994-10-21	항비루스 활성을 갖는 화합물의 제조방법
US4060616A (en)	1977-11-29	Purine derivatives with repeating unit
EP0531349A1 (fr)	1993-03-17	Derives de xanthine substitues en positions 1-7 possedant une activite anti-asthmatique, leurs sels acceptables sur le plan physiologique, composition pharmaceutique les contenant et procede de preparation
EP0366385A1 (fr)	1990-05-02	Dérivés de guanine ayant une activité anti-virale et leurs sels pharmaceutiquement acceptables
WO1998002166A1 (fr)	1998-01-22	Inhibiteurs de l'adenosine desaminase
DE69531555T2 (de)	2004-06-17	Dreifachsubstituierte thioxanthine
IE44708B1 (en)	1982-03-10	Esters of hydroxyalkoxylkyl purines, their preparation, and pharmaceutical compositions containing them
CS203095B2 (cs)	1981-02-27	Způsob přípravy substituovaných purinů