CA2216763A1 - N-acylpiperazine derivative, anti-ulcer drug, and antibacterial drug - Google Patents
N-acylpiperazine derivative, anti-ulcer drug, and antibacterial drug Download PDFInfo
- Publication number
- CA2216763A1 CA2216763A1 CA002216763A CA2216763A CA2216763A1 CA 2216763 A1 CA2216763 A1 CA 2216763A1 CA 002216763 A CA002216763 A CA 002216763A CA 2216763 A CA2216763 A CA 2216763A CA 2216763 A1 CA2216763 A1 CA 2216763A1
- Authority
- CA
- Canada
- Prior art keywords
- group
- compound
- salt
- acylpiperazine derivative
- acylpiperazine
- Prior art date
- Legal status (The legal status 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 status listed.)
- Abandoned
Links
- 239000003699 antiulcer agent Substances 0.000 title claims description 6
- 229940124350 antibacterial drug Drugs 0.000 title claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 36
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 33
- 150000003839 salts Chemical class 0.000 claims abstract description 30
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 19
- 241000589989 Helicobacter Species 0.000 claims abstract description 12
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims abstract description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 7
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 7
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 6
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims abstract description 6
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 5
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- 238000000034 method Methods 0.000 claims description 49
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- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
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- 239000002671 adjuvant Substances 0.000 claims description 4
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- 125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 208000007107 Stomach Ulcer Diseases 0.000 claims description 3
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- 230000017066 negative regulation of growth Effects 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 36
- 208000025865 Ulcer Diseases 0.000 abstract description 18
- 231100000397 ulcer Toxicity 0.000 abstract description 18
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- 229910001923 silver oxide Inorganic materials 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- VGTPCRGMBIAPIM-UHFFFAOYSA-M sodium thiocyanate Chemical compound [Na+].[S-]C#N VGTPCRGMBIAPIM-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 238000009495 sugar coating Methods 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 235000013337 tricalcium citrate Nutrition 0.000 description 1
- 210000005239 tubule Anatomy 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/192—Radicals derived from carboxylic acids from aromatic carboxylic acids
-
- 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
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- C07D213/80—Acids; Esters in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/62—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to atoms of the carbocyclic ring
- C07D317/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
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)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP27887296 | 1996-09-30 | ||
| JP8-278872 | 1996-09-30 | ||
| JP08593797A JP4189043B2 (ja) | 1996-09-30 | 1997-03-18 | Ｎ−アシルピペラジン誘導体及び抗菌剤、抗潰瘍剤 |
| JP9-85937 | 1997-03-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2216763A1 true CA2216763A1 (en) | 1998-03-30 |
Family
ID=26426951
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002216763A Abandoned CA2216763A1 (en) | 1996-09-30 | 1997-09-29 | N-acylpiperazine derivative, anti-ulcer drug, and antibacterial drug |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US5962456A (enExample) |
| EP (1) | EP0832887B1 (enExample) |
| JP (1) | JP4189043B2 (enExample) |
| KR (1) | KR19980025185A (enExample) |
| AT (1) | ATE203989T1 (enExample) |
| AU (1) | AU717312B2 (enExample) |
| CA (1) | CA2216763A1 (enExample) |
| DE (1) | DE69706012T2 (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19824865A1 (de) * | 1997-08-27 | 1999-03-04 | Solvay Pharm Gmbh | Neue Harnstoffderivate |
| ATE396187T1 (de) * | 1997-08-27 | 2008-06-15 | Solvay Pharm Gmbh | Indolmethyl-n,n'-bisacylpiperazine als neurokininrezeptorantagonisten |
| UA75425C2 (en) | 2001-07-09 | 2006-04-17 | Piperazine oxime derivatives with antagonistic activity to nk-1 receptor, use thereof, a pharmaceutical composition based thereon, a method for producing and a method for producing intermediary compounds |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB964232A (en) * | 1962-04-16 | 1964-07-22 | Analyses Et De Rech S Biolog M | Substituted benzamides and pharmaceutical compositions containing them |
| US4208205A (en) * | 1977-10-03 | 1980-06-17 | E. I. Du Pont De Nemours And Company | Herbicidal benzamides |
| JPS6058954A (ja) * | 1983-09-13 | 1985-04-05 | Kureha Chem Ind Co Ltd | ジヒドロキシベンズアミド誘導体 |
| US5143910A (en) * | 1989-09-07 | 1992-09-01 | Shionogi & Co., Ltd. | Piperaziniocephalosporins |
| HUT60458A (en) * | 1991-02-01 | 1992-09-28 | Sandoz Ag | Process for producing benzyloxyphenyl derivatives and pharmaceutical compositions comprising same |
| FR2701259B1 (fr) * | 1993-02-08 | 1995-03-24 | Rhone Poulenc Agrochimie | Procédé pour la préparation de dérivés phénylbenzamides fongicides agricoles. |
| JP3081773B2 (ja) * | 1995-03-31 | 2000-08-28 | 株式会社資生堂 | Ｎ−アシルピペラジン誘導体及び抗菌剤、抗潰瘍剤 |
-
1997
- 1997-03-18 JP JP08593797A patent/JP4189043B2/ja not_active Expired - Lifetime
- 1997-09-29 US US08/939,912 patent/US5962456A/en not_active Expired - Lifetime
- 1997-09-29 CA CA002216763A patent/CA2216763A1/en not_active Abandoned
- 1997-09-30 DE DE69706012T patent/DE69706012T2/de not_active Expired - Lifetime
- 1997-09-30 KR KR1019970051173A patent/KR19980025185A/ko not_active Withdrawn
- 1997-09-30 AT AT97307709T patent/ATE203989T1/de not_active IP Right Cessation
- 1997-09-30 EP EP97307709A patent/EP0832887B1/en not_active Expired - Lifetime
- 1997-09-30 AU AU39322/97A patent/AU717312B2/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| JPH10152487A (ja) | 1998-06-09 |
| KR19980025185A (ko) | 1998-07-06 |
| EP0832887A1 (en) | 1998-04-01 |
| DE69706012D1 (de) | 2001-09-13 |
| JP4189043B2 (ja) | 2008-12-03 |
| AU717312B2 (en) | 2000-03-23 |
| US5962456A (en) | 1999-10-05 |
| DE69706012T2 (de) | 2002-05-29 |
| ATE203989T1 (de) | 2001-08-15 |
| AU3932297A (en) | 1998-04-02 |
| EP0832887B1 (en) | 2001-08-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |