SK140799A3 - Spiro aminopyrimidines, process for their preparation, pharmaceutical compositions and their use - Google Patents
Spiro aminopyrimidines, process for their preparation, pharmaceutical compositions and their use Download PDFInfo
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- SK140799A3 SK140799A3 SK1407-99A SK140799A SK140799A3 SK 140799 A3 SK140799 A3 SK 140799A3 SK 140799 A SK140799 A SK 140799A SK 140799 A3 SK140799 A3 SK 140799A3
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- Slovakia
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- formula
- compound
- pharmaceutically acceptable
- acceptable salt
- tautomer
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- 239000008194 pharmaceutical composition Substances 0.000 title claims description 7
- -1 Spiro aminopyrimidines Chemical class 0.000 title claims description 5
- 238000000034 method Methods 0.000 title abstract description 24
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- 238000002360 preparation method Methods 0.000 title abstract description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 97
- 150000003839 salts Chemical class 0.000 claims abstract description 40
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- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims abstract description 12
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- 208000027866 inflammatory disease Diseases 0.000 claims abstract description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 8
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 7
- 102000008299 Nitric Oxide Synthase Human genes 0.000 claims abstract description 6
- 108010021487 Nitric Oxide Synthase Proteins 0.000 claims abstract description 6
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 6
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 5
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- OLALTCCCZUIPTQ-UHFFFAOYSA-N ethyl 7-aminospiro[4h-thieno[2,3-c]pyridine-5,4'-piperidine]-1'-carboxylate Chemical compound C1CN(C(=O)OCC)CCC21N=C(N)C(SC=C1)=C1C2 OLALTCCCZUIPTQ-UHFFFAOYSA-N 0.000 claims description 4
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- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 206010006451 bronchitis Diseases 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 208000016644 chronic atrophic gastritis Diseases 0.000 description 1
- 230000036461 convulsion Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 201000006549 dyspepsia Diseases 0.000 description 1
- 230000003511 endothelial effect Effects 0.000 description 1
- 206010015037 epilepsy Diseases 0.000 description 1
- AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 description 1
- YEJPJWOFYQBVSN-UHFFFAOYSA-N ethyl 1-oxa-6-azaspiro[2.5]octane-6-carboxylate Chemical compound C1CN(C(=O)OCC)CCC11OC1 YEJPJWOFYQBVSN-UHFFFAOYSA-N 0.000 description 1
- ZGVZIJJQHIHGLE-UHFFFAOYSA-N ethyl 5-fluoro-4-oxospiro[3H-1,3-benzoxazine-2,4'-piperidine]-1'-carboxylate Chemical compound C1CN(C(=O)OCC)CCC21OC1=CC=CC(F)=C1C(=O)N2 ZGVZIJJQHIHGLE-UHFFFAOYSA-N 0.000 description 1
- OYOAYZNAJQQPFS-UHFFFAOYSA-N ethyl 5-fluoro-4-sulfanylidenespiro[3h-1,3-benzoxazine-2,4'-piperidine]-1'-carboxylate Chemical compound C1CN(C(=O)OCC)CCC21OC1=CC=CC(F)=C1C(=S)N2 OYOAYZNAJQQPFS-UHFFFAOYSA-N 0.000 description 1
- WFCLYEAZTHWNEH-UHFFFAOYSA-N ethylthiocyanate Chemical compound CCSC#N WFCLYEAZTHWNEH-UHFFFAOYSA-N 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 208000022195 farmer lung disease Diseases 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 208000007565 gingivitis Diseases 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 208000024798 heartburn Diseases 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- VYXVPOVYYRXJCS-UHFFFAOYSA-N hydroxylamine;dihydrochloride Chemical compound Cl.Cl.ON VYXVPOVYYRXJCS-UHFFFAOYSA-N 0.000 description 1
- 230000002218 hypoglycaemic effect Effects 0.000 description 1
- 230000036543 hypotension Effects 0.000 description 1
- 210000000987 immune system Anatomy 0.000 description 1
- 230000001506 immunosuppresive effect Effects 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 229940047122 interleukins Drugs 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 1
- 150000002496 iodine Chemical class 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 208000002551 irritable bowel syndrome Diseases 0.000 description 1
- 208000028867 ischemia Diseases 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 208000033915 jet lag type circadian rhythm sleep disease Diseases 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- 210000002540 macrophage Anatomy 0.000 description 1
- 210000004962 mammalian cell Anatomy 0.000 description 1
- SJEGOBZCHQZVQJ-UHFFFAOYSA-M methanesulfonate;trimethylsulfanium Chemical compound C[S+](C)C.CS([O-])(=O)=O SJEGOBZCHQZVQJ-UHFFFAOYSA-M 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 206010027599 migraine Diseases 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000017074 necrotic cell death Effects 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
- 208000004296 neuralgia Diseases 0.000 description 1
- 208000015122 neurodegenerative disease Diseases 0.000 description 1
- 208000021722 neuropathic pain Diseases 0.000 description 1
- 239000002858 neurotransmitter agent Substances 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 201000008482 osteoarthritis Diseases 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 230000008506 pathogenesis Effects 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 208000024981 pyrosis Diseases 0.000 description 1
- 229910052705 radium Inorganic materials 0.000 description 1
- HCWPIIXVSYCSAN-UHFFFAOYSA-N radium atom Chemical compound [Ra] HCWPIIXVSYCSAN-UHFFFAOYSA-N 0.000 description 1
- 230000029865 regulation of blood pressure Effects 0.000 description 1
- 230000004648 relaxation of smooth muscle Effects 0.000 description 1
- 208000023504 respiratory system disease Diseases 0.000 description 1
- 201000000980 schizophrenia Diseases 0.000 description 1
- 208000012672 seasonal affective disease Diseases 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 208000019116 sleep disease Diseases 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 210000000278 spinal cord Anatomy 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 208000011117 substance-related disease Diseases 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D495/20—Spiro-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
- A61P11/06—Antiasthmatics
-
- 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
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/10—Spiro-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pain & Pain Management (AREA)
- Pulmonology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE9701396A SE9701396D0 (sv) | 1997-04-15 | 1997-04-15 | Compounds |
| PCT/SE1998/000642 WO1998046611A1 (en) | 1997-04-15 | 1998-04-07 | Compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK140799A3 true SK140799A3 (en) | 2000-05-16 |
Family
ID=20406574
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK1407-99A SK140799A3 (en) | 1997-04-15 | 1998-04-07 | Spiro aminopyrimidines, process for their preparation, pharmaceutical compositions and their use |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US6100246A (is) |
| EP (1) | EP0975639A1 (is) |
| JP (1) | JP2001521517A (is) |
| KR (1) | KR20010006349A (is) |
| CN (1) | CN1259132A (is) |
| AU (1) | AU7091198A (is) |
| BR (1) | BR9808546A (is) |
| CA (1) | CA2286789A1 (is) |
| EE (1) | EE9900466A (is) |
| HU (1) | HUP0002245A3 (is) |
| ID (1) | ID23812A (is) |
| IL (1) | IL132272A0 (is) |
| IS (1) | IS5211A (is) |
| NO (1) | NO995007L (is) |
| NZ (1) | NZ338007A (is) |
| PL (1) | PL336318A1 (is) |
| SE (1) | SE9701396D0 (is) |
| SK (1) | SK140799A3 (is) |
| TR (1) | TR199902537T2 (is) |
| WO (1) | WO1998046611A1 (is) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000024746A1 (de) * | 1998-10-27 | 2000-05-04 | Schering Aktiengesellschaft | Thienooxazine als nos-hemmer |
| US20040009940A1 (en) * | 2000-10-20 | 2004-01-15 | Coleman Michael E. | Gene delivery formulations and methods for treatment of ischemic conditions |
| JP4537024B2 (ja) * | 2003-08-06 | 2010-09-01 | 株式会社琉球バイオリソース開発 | 炎症疾患予防・治療剤 |
| JO3126B1 (ar) * | 2007-11-14 | 2017-09-20 | Janssen Pharmaceutica Nv | مثبطات ناقل نيوكليوسيد متوازن اي ان تي 1 |
| CA3209491A1 (en) | 2021-03-15 | 2022-09-22 | Saul Yedgar | Hyaluronic acid-conjugated dipalmitoyl phosphatidyl ethanolamine in combination with non-steroidal anti-inflammatory drugs (nsaids) for treating or alleviating inflammatory disease |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3686187A (en) * | 1970-05-25 | 1972-08-22 | Abbott Lab | 4-anilino-1-(4-p-fluorophenyl-1-butyl) piperidine compounds |
| US4092414A (en) * | 1975-04-25 | 1978-05-30 | Merck & Co., Inc. | 3,4-Dihydrospiro-2H-1,3-benzoxazines and their use in treating edema, abnormal electrolyte retention, and inflammation |
| EP0189370A3 (de) * | 1985-01-16 | 1988-01-27 | Sandoz Ag | Spiro-dioxolane, -dithiolane und -oxothiolane |
| DE4315625A1 (de) * | 1993-05-11 | 1994-11-17 | Hoechst Ag | Neue Derivate des 3-Fluorphenols, Verfahren zu ihrer Herstellung und ihre Verwendung |
-
1997
- 1997-04-15 SE SE9701396A patent/SE9701396D0/xx unknown
-
1998
- 1998-04-07 KR KR1019997009434A patent/KR20010006349A/ko not_active Withdrawn
- 1998-04-07 WO PCT/SE1998/000642 patent/WO1998046611A1/en not_active Ceased
- 1998-04-07 IL IL13227298A patent/IL132272A0/xx unknown
- 1998-04-07 NZ NZ338007A patent/NZ338007A/en unknown
- 1998-04-07 TR TR1999/02537T patent/TR199902537T2/xx unknown
- 1998-04-07 US US09/068,469 patent/US6100246A/en not_active Expired - Fee Related
- 1998-04-07 PL PL98336318A patent/PL336318A1/xx unknown
- 1998-04-07 JP JP54380498A patent/JP2001521517A/ja active Pending
- 1998-04-07 CN CN98805909A patent/CN1259132A/zh active Pending
- 1998-04-07 EE EEP199900466A patent/EE9900466A/xx unknown
- 1998-04-07 HU HU0002245A patent/HUP0002245A3/hu unknown
- 1998-04-07 CA CA002286789A patent/CA2286789A1/en not_active Abandoned
- 1998-04-07 AU AU70911/98A patent/AU7091198A/en not_active Abandoned
- 1998-04-07 SK SK1407-99A patent/SK140799A3/sk unknown
- 1998-04-07 BR BR9808546-8A patent/BR9808546A/pt not_active IP Right Cessation
- 1998-04-07 EP EP98917861A patent/EP0975639A1/en not_active Withdrawn
- 1998-07-04 ID IDW991161A patent/ID23812A/id unknown
-
1999
- 1999-10-12 IS IS5211A patent/IS5211A/is unknown
- 1999-10-14 NO NO995007A patent/NO995007L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| WO1998046611A1 (en) | 1998-10-22 |
| CN1259132A (zh) | 2000-07-05 |
| JP2001521517A (ja) | 2001-11-06 |
| TR199902537T2 (xx) | 2000-02-21 |
| US6100246A (en) | 2000-08-08 |
| BR9808546A (pt) | 2000-05-23 |
| KR20010006349A (ko) | 2001-01-26 |
| PL336318A1 (en) | 2000-06-19 |
| EP0975639A1 (en) | 2000-02-02 |
| CA2286789A1 (en) | 1998-10-22 |
| IL132272A0 (en) | 2001-03-19 |
| HUP0002245A3 (en) | 2001-06-28 |
| IS5211A (is) | 1999-10-12 |
| ID23812A (id) | 2000-05-11 |
| NO995007L (no) | 1999-12-14 |
| NZ338007A (en) | 2001-05-25 |
| EE9900466A (et) | 2000-04-17 |
| SE9701396D0 (sv) | 1997-04-15 |
| AU7091198A (en) | 1998-11-11 |
| NO995007D0 (no) | 1999-10-14 |
| HUP0002245A2 (hu) | 2001-05-28 |
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