DE2722772A1 - Neue imidazobenzoxazinderivate, ihre salze, verfahren zu deren herstellung und arzneimittel - Google Patents
Neue imidazobenzoxazinderivate, ihre salze, verfahren zu deren herstellung und arzneimittelInfo
- Publication number
- DE2722772A1 DE2722772A1 DE19772722772 DE2722772A DE2722772A1 DE 2722772 A1 DE2722772 A1 DE 2722772A1 DE 19772722772 DE19772722772 DE 19772722772 DE 2722772 A DE2722772 A DE 2722772A DE 2722772 A1 DE2722772 A1 DE 2722772A1
- Authority
- DE
- Germany
- Prior art keywords
- formula
- group
- compound
- coor
- salts
- 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.)
- Withdrawn
Links
- 150000003839 salts Chemical class 0.000 title claims description 40
- 238000000034 method Methods 0.000 title claims description 22
- UCCWJUWUHMVASJ-UHFFFAOYSA-N imidazo[4,5-h][1,2]benzoxazine Chemical class C1=CC2=CC=NOC2=C2C1=NC=N2 UCCWJUWUHMVASJ-UHFFFAOYSA-N 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title description 4
- 229940126601 medicinal product Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 97
- -1 alkyl radical Chemical class 0.000 claims description 51
- 125000004432 carbon atom Chemical group C* 0.000 claims description 33
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 31
- 239000002253 acid Substances 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 229910052740 iodine Inorganic materials 0.000 claims description 9
- 125000003277 amino group Chemical group 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
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- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 230000000802 nitrating effect Effects 0.000 claims description 2
- 125000006239 protecting group Chemical group 0.000 claims description 2
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 1
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- 229960003116 amyl nitrite Drugs 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
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- 229910052751 metal Inorganic materials 0.000 description 3
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- CSDTZUBPSYWZDX-UHFFFAOYSA-N n-pentyl nitrite Chemical compound CCCCCON=O CSDTZUBPSYWZDX-UHFFFAOYSA-N 0.000 description 3
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- 239000002244 precipitate Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 3
- MAWVXTXVSFHOLJ-UHFFFAOYSA-N 2h-1,4-benzoxazine-2-carboxylic acid Chemical compound C1=CC=C2N=CC(C(=O)O)OC2=C1 MAWVXTXVSFHOLJ-UHFFFAOYSA-N 0.000 description 2
- VVHVOAHQUDZCMD-UHFFFAOYSA-N 4h-imidazo[2,1-c][1,4]benzoxazine-2-carboxylic acid Chemical compound C1=CC=C2N3C=C(C(=O)O)N=C3COC2=C1 VVHVOAHQUDZCMD-UHFFFAOYSA-N 0.000 description 2
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- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 235000011087 fumaric acid Nutrition 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229910000043 hydrogen iodide Inorganic materials 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000003550 marker Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
- JNZHKHLCSPCGCO-UHFFFAOYSA-N methyl 4h-imidazo[2,1-c][1,4]benzoxazine-2-carboxylate Chemical compound C1=CC=C2N3C=C(C(=O)OC)N=C3COC2=C1 JNZHKHLCSPCGCO-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229940105631 nembutal Drugs 0.000 description 1
- 239000002687 nonaqueous vehicle Substances 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 210000001672 ovary Anatomy 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 210000003899 penis Anatomy 0.000 description 1
- WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000002904 solvent 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
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000007940 sugar coated tablet Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 229960000281 trometamol Drugs 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
- C07D265/34—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings
- C07D265/36—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings condensed with one six-membered ring
-
- 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
- A61P11/08—Bronchodilators
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Pulmonology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Immunology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB21111/76A GB1538479A (en) | 1976-05-21 | 1976-05-21 | Imidazobenzoxazines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2722772A1 true DE2722772A1 (de) | 1977-12-08 |
Family
ID=10157418
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19772722772 Withdrawn DE2722772A1 (de) | 1976-05-21 | 1977-05-20 | Neue imidazobenzoxazinderivate, ihre salze, verfahren zu deren herstellung und arzneimittel |
Country Status (10)
| Country | Link |
|---|---|
| JP (1) | JPS6045199B2 (enExample) |
| BE (1) | BE854850A (enExample) |
| CA (1) | CA1100963A (enExample) |
| CH (2) | CH624118A5 (enExample) |
| DE (1) | DE2722772A1 (enExample) |
| DK (1) | DK216977A (enExample) |
| FR (1) | FR2351980A1 (enExample) |
| GB (1) | GB1538479A (enExample) |
| IE (1) | IE44905B1 (enExample) |
| NL (1) | NL7705614A (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2710571A1 (de) * | 1976-03-29 | 1977-10-13 | United States Borax Chem | Herbicid wirksame morpholinobenzimidazole, sie enthaltendes herbicides mittel und ihre verwendung zum bekaempfen des wachstums von unkraut |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE444319B (sv) * | 1977-11-18 | 1986-04-07 | Roussel Uclaf | Nya imidazobensoxazinderivat, forfarande for framstellning derav och farmaceutiska kompositioner innehallande dessa foreningar |
| SE439308B (sv) * | 1978-08-02 | 1985-06-10 | Roussel Uclaf | Imidazo(1,2-a)kinoxaliner och farmaceutiska kompositioner derav |
| IL59104A (en) * | 1979-02-09 | 1984-02-29 | Roussel Uclaf | Heterotricyclic derivatives,process for their preparation and pharmaceutical compositions incorporating them |
| US5329012A (en) * | 1987-10-29 | 1994-07-12 | The Research Foundation Of State University Of New York | Bis(acyloxmethyl)imidazole compounds |
| GB9212486D0 (en) * | 1992-06-12 | 1992-07-22 | Erba Carlo Spa | Derivatives of substituted imidazo benzoxazin-1-one and process for their preparation |
| JP6705262B2 (ja) * | 2016-04-04 | 2020-06-03 | 三菱ケミカル株式会社 | アニオン硬化性化合物用硬化剤、硬化性組成物、および硬化物 |
-
1976
- 1976-05-21 GB GB21111/76A patent/GB1538479A/en not_active Expired
-
1977
- 1977-05-18 DK DK216977A patent/DK216977A/da not_active Application Discontinuation
- 1977-05-18 FR FR7715294A patent/FR2351980A1/fr active Granted
- 1977-05-20 CH CH623277A patent/CH624118A5/fr not_active IP Right Cessation
- 1977-05-20 DE DE19772722772 patent/DE2722772A1/de not_active Withdrawn
- 1977-05-20 CA CA278,863A patent/CA1100963A/fr not_active Expired
- 1977-05-20 BE BE177750A patent/BE854850A/xx unknown
- 1977-05-20 JP JP52057812A patent/JPS6045199B2/ja not_active Expired
- 1977-05-20 NL NL7705614A patent/NL7705614A/xx not_active Application Discontinuation
- 1977-05-23 IE IE1052/77A patent/IE44905B1/en unknown
-
1980
- 1980-09-04 CH CH666280A patent/CH623053A5/fr not_active IP Right Cessation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2710571A1 (de) * | 1976-03-29 | 1977-10-13 | United States Borax Chem | Herbicid wirksame morpholinobenzimidazole, sie enthaltendes herbicides mittel und ihre verwendung zum bekaempfen des wachstums von unkraut |
Also Published As
| Publication number | Publication date |
|---|---|
| NL7705614A (nl) | 1977-11-23 |
| FR2351980A1 (fr) | 1977-12-16 |
| CH624118A5 (en) | 1981-07-15 |
| GB1538479A (en) | 1979-01-17 |
| DK216977A (da) | 1977-11-22 |
| FR2351980B1 (enExample) | 1980-03-07 |
| CA1100963A (fr) | 1981-05-12 |
| JPS52156899A (en) | 1977-12-27 |
| CH623053A5 (en) | 1981-05-15 |
| IE44905L (en) | 1982-05-05 |
| IE44905B1 (en) | 1982-05-05 |
| JPS6045199B2 (ja) | 1985-10-08 |
| BE854850A (fr) | 1977-11-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| 8128 | New person/name/address of the agent |
Representative=s name: ZUMSTEIN SEN., F., DR. ASSMANN, E., DIPL.-CHEM. DR |
|
| 8130 | Withdrawal |