DE2227489A1 - Substituierte (5,6,e)Oxazinindole, Verfahren zu ihrer Herstellung und ihre Verwendung als oder in pharmazeutischen Präparaten - Google Patents
Substituierte (5,6,e)Oxazinindole, Verfahren zu ihrer Herstellung und ihre Verwendung als oder in pharmazeutischen PräparatenInfo
- Publication number
- DE2227489A1 DE2227489A1 DE19722227489 DE2227489A DE2227489A1 DE 2227489 A1 DE2227489 A1 DE 2227489A1 DE 19722227489 DE19722227489 DE 19722227489 DE 2227489 A DE2227489 A DE 2227489A DE 2227489 A1 DE2227489 A1 DE 2227489A1
- Authority
- DE
- Germany
- Prior art keywords
- formula
- substituted
- radical
- carbon atoms
- pharmaceutical preparations
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 6
- 239000000825 pharmaceutical preparation Substances 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 3
- JPSRLTQMTXQKAL-UHFFFAOYSA-N 1h-indole;2h-oxazine Chemical class N1OC=CC=C1.C1=CC=C2NC=CC2=C1 JPSRLTQMTXQKAL-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 23
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 208000002193 Pain Diseases 0.000 claims description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 3
- 206010020772 Hypertension Diseases 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 229960004279 formaldehyde Drugs 0.000 claims description 2
- 235000019256 formaldehyde Nutrition 0.000 claims description 2
- -1 cycloalkyl radical Chemical class 0.000 claims 2
- 150000003254 radicals Chemical class 0.000 claims 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 206010017999 Gastrointestinal pain Diseases 0.000 claims 1
- YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical compound [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 claims 1
- 230000000241 respiratory effect Effects 0.000 claims 1
- 230000000694 effects Effects 0.000 description 6
- XQYZDYMELSJDRZ-UHFFFAOYSA-N papaverine Chemical compound C1=C(OC)C(OC)=CC=C1CC1=NC=CC2=CC(OC)=C(OC)C=C12 XQYZDYMELSJDRZ-UHFFFAOYSA-N 0.000 description 6
- 206010030113 Oedema Diseases 0.000 description 4
- 229930008281 A03AD01 - Papaverine Natural products 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 208000007101 Muscle Cramp Diseases 0.000 description 3
- 208000005392 Spasm Diseases 0.000 description 3
- 229960001789 papaverine Drugs 0.000 description 3
- 208000023504 respiratory system disease Diseases 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- 206010065929 Cardiovascular insufficiency Diseases 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 230000001077 hypotensive effect Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- 241000252185 Cobitidae Species 0.000 description 1
- 208000001953 Hypotension Diseases 0.000 description 1
- 206010065390 Inflammatory pain Diseases 0.000 description 1
- 241000187479 Mycobacterium tuberculosis Species 0.000 description 1
- 208000004880 Polyuria Diseases 0.000 description 1
- 208000004756 Respiratory Insufficiency Diseases 0.000 description 1
- 206010038678 Respiratory depression Diseases 0.000 description 1
- DXGTUUQHTDOFFQ-UHFFFAOYSA-N [N].C1=CC=C2NC=CC2=C1 Chemical group [N].C1=CC=C2NC=CC2=C1 DXGTUUQHTDOFFQ-UHFFFAOYSA-N 0.000 description 1
- MPMBKUONVWADBW-UHFFFAOYSA-N [N].O1NC=CC=C1 Chemical group [N].O1NC=CC=C1 MPMBKUONVWADBW-UHFFFAOYSA-N 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000002365 anti-tubercular Effects 0.000 description 1
- 230000004872 arterial blood pressure Effects 0.000 description 1
- WDIHJSXYQDMJHN-UHFFFAOYSA-L barium chloride Chemical compound [Cl-].[Cl-].[Ba+2] WDIHJSXYQDMJHN-UHFFFAOYSA-L 0.000 description 1
- 229910001626 barium chloride Inorganic materials 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 210000004351 coronary vessel Anatomy 0.000 description 1
- 230000002089 crippling effect Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000010339 dilation Effects 0.000 description 1
- 230000035619 diuresis Effects 0.000 description 1
- 239000002934 diuretic Substances 0.000 description 1
- 230000001882 diuretic effect Effects 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 210000001198 duodenum Anatomy 0.000 description 1
- BSNHKSUAAMJXBB-UHFFFAOYSA-N ethyl 5-hydroxy-2-methyl-1h-indole-3-carboxylate Chemical compound C1=C(O)C=C2C(C(=O)OCC)=C(C)NC2=C1 BSNHKSUAAMJXBB-UHFFFAOYSA-N 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- 208000021822 hypotensive Diseases 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229960005181 morphine Drugs 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000000793 phophlogistic effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000036387 respiratory rate Effects 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 230000000304 vasodilatating effect Effects 0.000 description 1
- 210000001835 viscera Anatomy 0.000 description 1
Classifications
-
- 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
- C07D498/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (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 |
|---|---|---|---|
| FR7120708A FR2140280B1 (enExample) | 1971-06-08 | 1971-06-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2227489A1 true DE2227489A1 (de) | 1972-12-28 |
Family
ID=9078293
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722227489 Pending DE2227489A1 (de) | 1971-06-08 | 1972-06-06 | Substituierte (5,6,e)Oxazinindole, Verfahren zu ihrer Herstellung und ihre Verwendung als oder in pharmazeutischen Präparaten |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US3852284A (enExample) |
| JP (1) | JPS5238B1 (enExample) |
| BE (1) | BE784197A (enExample) |
| CA (1) | CA989836A (enExample) |
| CH (1) | CH533131A (enExample) |
| DE (1) | DE2227489A1 (enExample) |
| ES (1) | ES403547A1 (enExample) |
| FR (1) | FR2140280B1 (enExample) |
| GB (1) | GB1333358A (enExample) |
| IT (1) | IT1051602B (enExample) |
| LU (1) | LU65464A1 (enExample) |
| NL (1) | NL160565C (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0263352A1 (de) * | 1986-10-04 | 1988-04-13 | Dr. Karl Thomae GmbH | Neue Imidazo-benzoxazinone, ihre Herstellung und diese Verbindungen enthaltende Arzneimittel |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4012511A (en) * | 1974-05-28 | 1977-03-15 | Ayerst Mckenna & Harrison Ltd. | Oxazinoindole derivatives useful as antidepressants |
-
1971
- 1971-06-08 FR FR7120708A patent/FR2140280B1/fr not_active Expired
-
1972
- 1972-05-31 BE BE784197A patent/BE784197A/xx unknown
- 1972-05-31 GB GB2537172A patent/GB1333358A/en not_active Expired
- 1972-06-02 CH CH821372A patent/CH533131A/fr not_active IP Right Cessation
- 1972-06-05 LU LU65464A patent/LU65464A1/xx unknown
- 1972-06-06 DE DE19722227489 patent/DE2227489A1/de active Pending
- 1972-06-06 ES ES403547A patent/ES403547A1/es not_active Expired
- 1972-06-06 US US00260298A patent/US3852284A/en not_active Expired - Lifetime
- 1972-06-07 NL NL7207695.A patent/NL160565C/xx active
- 1972-06-07 JP JP47056119A patent/JPS5238B1/ja active Pending
- 1972-06-07 IT IT68803/72A patent/IT1051602B/it active
- 1972-06-08 CA CA144,274A patent/CA989836A/fr not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0263352A1 (de) * | 1986-10-04 | 1988-04-13 | Dr. Karl Thomae GmbH | Neue Imidazo-benzoxazinone, ihre Herstellung und diese Verbindungen enthaltende Arzneimittel |
| US4831027A (en) * | 1986-10-04 | 1989-05-16 | Dr. Karl Thomae Gmbh | Imidazo-benzoxazinones, the preparation thereof and pharmaceutical compositions containing these compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| LU65464A1 (enExample) | 1973-01-22 |
| FR2140280B1 (enExample) | 1974-08-23 |
| JPS5238B1 (enExample) | 1977-01-05 |
| NL160565C (nl) | 1979-11-15 |
| IT1051602B (it) | 1981-05-20 |
| GB1333358A (en) | 1973-10-10 |
| ES403547A1 (es) | 1975-05-01 |
| BE784197A (fr) | 1972-11-30 |
| CH533131A (fr) | 1973-01-31 |
| CA989836A (fr) | 1976-05-25 |
| FR2140280A1 (enExample) | 1973-01-19 |
| NL160565B (nl) | 1979-06-15 |
| NL7207695A (enExample) | 1972-12-12 |
| US3852284A (en) | 1974-12-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHW | Rejection |