NO302887B1 - Sakkarinderivater med proteolytisk enzyminhiberende aktivitet, farmasöytisk preparat inneholdende slike derivater samt anvendelse derav - Google Patents
Sakkarinderivater med proteolytisk enzyminhiberende aktivitet, farmasöytisk preparat inneholdende slike derivater samt anvendelse derav Download PDFInfo
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- NO302887B1 NO302887B1 NO924402A NO924402A NO302887B1 NO 302887 B1 NO302887 B1 NO 302887B1 NO 924402 A NO924402 A NO 924402A NO 924402 A NO924402 A NO 924402A NO 302887 B1 NO302887 B1 NO 302887B1
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- Norway
- Prior art keywords
- compound
- formula
- isopropyl
- methoxysaccharin
- saccharin
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- 102000035195 Peptidases Human genes 0.000 title claims description 11
- 108091005804 Peptidases Proteins 0.000 title claims description 11
- 230000002401 inhibitory effect Effects 0.000 title claims description 6
- 239000000825 pharmaceutical preparation Substances 0.000 title claims description 6
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical class C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 title description 15
- 150000001875 compounds Chemical class 0.000 claims description 75
- -1 1-phenyltetrazol-5-yl Chemical group 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 10
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- 150000003839 salts Chemical class 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 6
- 125000000524 functional group Chemical group 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 2
- 229940126601 medicinal product Drugs 0.000 claims 1
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- 229940081974 saccharin Drugs 0.000 description 12
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- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 12
- 238000009833 condensation Methods 0.000 description 11
- 230000005494 condensation Effects 0.000 description 11
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- 239000001257 hydrogen Substances 0.000 description 11
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- PJAVQIHLFGIEMQ-UHFFFAOYSA-N 2-[[4,5-bis(tert-butylsulfonyl)triazol-1-yl]methyl]-6-methoxy-1,1-dioxo-4-propan-2-yl-1,2-benzothiazol-3-one Chemical compound CC(C)C1=CC(OC)=CC(S2(=O)=O)=C1C(=O)N2CN1N=NC(S(=O)(=O)C(C)(C)C)=C1S(=O)(=O)C(C)(C)C PJAVQIHLFGIEMQ-UHFFFAOYSA-N 0.000 description 1
- IVANFNGOSJTZFM-UHFFFAOYSA-N 2h-triazole-4,5-dicarbonitrile Chemical compound N#CC1=NNN=C1C#N IVANFNGOSJTZFM-UHFFFAOYSA-N 0.000 description 1
- HDIBQANHVXCQBC-UHFFFAOYSA-N 2h-triazole-4,5-dicarboxamide Chemical compound NC(=O)C1=NNN=C1C(N)=O HDIBQANHVXCQBC-UHFFFAOYSA-N 0.000 description 1
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- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
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- 239000003054 catalyst Substances 0.000 description 1
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- 238000007265 chloromethylation reaction Methods 0.000 description 1
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- 208000007451 chronic bronchitis Diseases 0.000 description 1
- 229960002376 chymotrypsin Drugs 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
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- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
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- 230000003412 degenerative effect Effects 0.000 description 1
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- 239000012954 diazonium Substances 0.000 description 1
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- NPOMSUOUAZCMBL-UHFFFAOYSA-N dichloromethane;ethoxyethane Chemical compound ClCCl.CCOCC NPOMSUOUAZCMBL-UHFFFAOYSA-N 0.000 description 1
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- HNGGSWPHMZXFNN-UHFFFAOYSA-N dimethyl 2h-triazole-4,5-dicarboxylate Chemical compound COC(=O)C1=NNN=C1C(=O)OC HNGGSWPHMZXFNN-UHFFFAOYSA-N 0.000 description 1
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- 150000004702 methyl esters Chemical class 0.000 description 1
- IZUSLUJUTFMNLS-UHFFFAOYSA-N n,n-diethyl-4-methoxy-2-propan-2-yl-6-sulfamoylbenzamide Chemical compound CCN(CC)C(=O)C1=C(C(C)C)C=C(OC)C=C1S(N)(=O)=O IZUSLUJUTFMNLS-UHFFFAOYSA-N 0.000 description 1
- IDNGNZOXBMVMLM-UHFFFAOYSA-N n,n-diethyl-4-methoxy-2-propan-2-ylbenzamide Chemical compound CCN(CC)C(=O)C1=CC=C(OC)C=C1C(C)C IDNGNZOXBMVMLM-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
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- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 230000017854 proteolysis Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
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- 230000007420 reactivation Effects 0.000 description 1
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- 210000003296 saliva Anatomy 0.000 description 1
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- 229910052708 sodium Inorganic materials 0.000 description 1
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- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007909 solid dosage form Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- NBNBICNWNFQDDD-UHFFFAOYSA-N sulfuryl dibromide Chemical compound BrS(Br)(=O)=O NBNBICNWNFQDDD-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 125000003396 thiol group Chemical class [H]S* 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 description 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
- 239000002753 trypsin inhibitor Substances 0.000 description 1
- JABYJIQOLGWMQW-UHFFFAOYSA-N undec-4-ene Chemical compound CCCCCCC=CCCC JABYJIQOLGWMQW-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
- C07D275/04—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings condensed with carbocyclic rings or ring systems
- C07D275/06—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings condensed with carbocyclic rings or ring systems with hetero atoms directly attached to the ring sulfur atom
-
- 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
- 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
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US79303591A | 1991-11-15 | 1991-11-15 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO924402D0 NO924402D0 (no) | 1992-11-13 |
| NO924402L NO924402L (no) | 1993-05-18 |
| NO302887B1 true NO302887B1 (no) | 1998-05-04 |
Family
ID=25158888
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO924402A NO302887B1 (no) | 1991-11-15 | 1992-11-13 | Sakkarinderivater med proteolytisk enzyminhiberende aktivitet, farmasöytisk preparat inneholdende slike derivater samt anvendelse derav |
Country Status (15)
| Country | Link |
|---|---|
| EP (1) | EP0542371A1 (de) |
| JP (1) | JPH06122675A (de) |
| KR (1) | KR930010016A (de) |
| AU (1) | AU656027B2 (de) |
| CA (1) | CA2082774A1 (de) |
| CZ (1) | CZ338892A3 (de) |
| FI (1) | FI925166A (de) |
| HU (2) | HUT65694A (de) |
| IL (1) | IL103747A (de) |
| MX (1) | MX9206568A (de) |
| NO (1) | NO302887B1 (de) |
| NZ (1) | NZ245126A (de) |
| RU (1) | RU2114835C1 (de) |
| SG (1) | SG52778A1 (de) |
| TW (1) | TW282463B (de) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5308938A (en) * | 1990-07-18 | 1994-05-03 | Otis Elevator Company | Elevator active suspension system |
| US5322144A (en) * | 1990-07-18 | 1994-06-21 | Otis Elevator Company | Active control of elevator platform |
| US5321217A (en) * | 1990-07-18 | 1994-06-14 | Otis Elevator Company | Apparatus and method for controlling an elevator horizontal suspension |
| US5294757A (en) * | 1990-07-18 | 1994-03-15 | Otis Elevator Company | Active vibration control system for an elevator, which reduces horizontal and rotational forces acting on the car |
| US5306818A (en) * | 1990-11-01 | 1994-04-26 | Sterling Winthrop Inc. | Tetrahydro 2-saccharinylmerthyl aryl carboxylates |
| AU668694B2 (en) * | 1991-12-19 | 1996-05-16 | Sanofi-Synthelabo | Saccharin derivative proteolytic enzyme inhibitors |
| US5378720A (en) * | 1991-12-19 | 1995-01-03 | Sterling Winthrop Inc. | Saccharin derivative proteolytic enzyme inhibitors |
| TW226016B (de) * | 1991-12-30 | 1994-07-01 | Sterling Winthrop Inc | |
| DE19533643A1 (de) * | 1995-09-12 | 1997-03-13 | Nycomed Arzneimittel Gmbh | Neue cyclische Derivate von Benzolsulfonamiden |
| WO2001017501A1 (en) * | 1999-09-10 | 2001-03-15 | The Procter & Gamble Company | Enzyme inhibitors |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2110414T3 (es) * | 1989-05-04 | 1998-02-16 | Sanofi Sa | Derivados de sacarina utiles como inhibidores de enzimas proteoliticas y su preparacion. |
| US5236917A (en) * | 1989-05-04 | 1993-08-17 | Sterling Winthrop Inc. | Saccharin derivatives useful as proteolytic enzyme inhibitors and compositions and method of use thereof |
| DE3917597A1 (de) * | 1989-05-26 | 1990-11-29 | Schering Ag | Neue leukotrien-b(pfeil abwaerts)4(pfeil abwaerts)-derivate, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
| AU642537B2 (en) * | 1990-11-01 | 1993-10-21 | Sanofi | 2-saccharinylmethyl aryl carboxylates useful as proteolytic enzyme inhibitors and compositions and method of use thereof |
-
1992
- 1992-09-30 AU AU26057/92A patent/AU656027B2/en not_active Ceased
- 1992-09-30 TW TW081107772A patent/TW282463B/zh active
- 1992-11-12 CA CA002082774A patent/CA2082774A1/en not_active Abandoned
- 1992-11-12 EP EP92203468A patent/EP0542371A1/de not_active Withdrawn
- 1992-11-12 SG SG1996009394A patent/SG52778A1/en unknown
- 1992-11-13 FI FI925166A patent/FI925166A/fi not_active Application Discontinuation
- 1992-11-13 CZ CS923388A patent/CZ338892A3/cs unknown
- 1992-11-13 HU HU9203561A patent/HUT65694A/hu unknown
- 1992-11-13 MX MX9206568A patent/MX9206568A/es unknown
- 1992-11-13 NO NO924402A patent/NO302887B1/no unknown
- 1992-11-13 IL IL103747A patent/IL103747A/en not_active IP Right Cessation
- 1992-11-13 RU RU92004409A patent/RU2114835C1/ru active
- 1992-11-13 NZ NZ245126A patent/NZ245126A/en unknown
- 1992-11-14 KR KR1019920021438A patent/KR930010016A/ko not_active Application Discontinuation
- 1992-11-16 JP JP4305222A patent/JPH06122675A/ja not_active Withdrawn
-
1995
- 1995-06-30 HU HU95P/P00612P patent/HU211664A9/hu unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NO924402L (no) | 1993-05-18 |
| FI925166A0 (fi) | 1992-11-13 |
| NO924402D0 (no) | 1992-11-13 |
| HUT65694A (en) | 1994-07-28 |
| CA2082774A1 (en) | 1993-05-16 |
| AU656027B2 (en) | 1995-01-19 |
| HU211664A9 (en) | 1995-12-28 |
| HU9203561D0 (en) | 1993-01-28 |
| IL103747A (en) | 1998-06-15 |
| AU2605792A (en) | 1993-05-20 |
| SG52778A1 (en) | 1998-09-28 |
| CZ338892A3 (en) | 1993-06-16 |
| JPH06122675A (ja) | 1994-05-06 |
| IL103747A0 (en) | 1993-04-04 |
| NZ245126A (en) | 1996-01-26 |
| EP0542371A1 (de) | 1993-05-19 |
| RU2114835C1 (ru) | 1998-07-10 |
| MX9206568A (es) | 1993-05-01 |
| FI925166A (fi) | 1993-05-16 |
| TW282463B (de) | 1996-08-01 |
| KR930010016A (ko) | 1993-06-21 |
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