DE2408603A1 - Substituierte (5,6,e)oxazinindole, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel - Google Patents
Substituierte (5,6,e)oxazinindole, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittelInfo
- Publication number
- DE2408603A1 DE2408603A1 DE19742408603 DE2408603A DE2408603A1 DE 2408603 A1 DE2408603 A1 DE 2408603A1 DE 19742408603 DE19742408603 DE 19742408603 DE 2408603 A DE2408603 A DE 2408603A DE 2408603 A1 DE2408603 A1 DE 2408603A1
- Authority
- DE
- Germany
- Prior art keywords
- general formula
- radical
- methyl
- substituted
- compounds
- 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
- 150000001875 compounds Chemical class 0.000 title claims description 34
- -1 OXAZINE INDOLES Chemical class 0.000 title claims description 21
- 229940126601 medicinal product Drugs 0.000 title description 2
- 238000004519 manufacturing process Methods 0.000 title 1
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims description 8
- JPSRLTQMTXQKAL-UHFFFAOYSA-N 1h-indole;2h-oxazine Chemical class N1OC=CC=C1.C1=CC=C2NC=CC2=C1 JPSRLTQMTXQKAL-UHFFFAOYSA-N 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- AJWSCYJIOFQSEJ-UHFFFAOYSA-N propan-2-yl 5-hydroxy-2-methyl-1h-indole-3-carboxylate Chemical compound C1=C(O)C=C2C(C(=O)OC(C)C)=C(C)NC2=C1 AJWSCYJIOFQSEJ-UHFFFAOYSA-N 0.000 claims description 4
- DDAGREFLDWPKEQ-UHFFFAOYSA-N butyl 5-hydroxy-2-methyl-1h-indole-3-carboxylate Chemical compound C1=C(O)C=C2C(C(=O)OCCCC)=C(C)NC2=C1 DDAGREFLDWPKEQ-UHFFFAOYSA-N 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- MZVQCMJNVPIDEA-UHFFFAOYSA-N [CH2]CN(CC)CC Chemical group [CH2]CN(CC)CC MZVQCMJNVPIDEA-UHFFFAOYSA-N 0.000 claims description 2
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 239000000700 radioactive tracer Substances 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 claims 1
- 208000002193 Pain Diseases 0.000 description 7
- 230000036407 pain Effects 0.000 description 7
- 206010030113 Oedema Diseases 0.000 description 5
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 4
- 206010020772 Hypertension Diseases 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 230000001882 diuretic effect Effects 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 208000025865 Ulcer Diseases 0.000 description 3
- 230000000202 analgesic effect Effects 0.000 description 3
- 230000003276 anti-hypertensive effect Effects 0.000 description 3
- 230000003110 anti-inflammatory effect Effects 0.000 description 3
- 230000000767 anti-ulcer Effects 0.000 description 3
- 239000002934 diuretic Substances 0.000 description 3
- 230000001624 sedative effect Effects 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- 231100000397 ulcer Toxicity 0.000 description 3
- 210000002700 urine Anatomy 0.000 description 3
- 208000019901 Anxiety disease Diseases 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- 206010029216 Nervousness Diseases 0.000 description 2
- 208000008469 Peptic Ulcer Diseases 0.000 description 2
- 208000004880 Polyuria Diseases 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 230000036506 anxiety Effects 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 230000035619 diuresis Effects 0.000 description 2
- 239000008098 formaldehyde solution Substances 0.000 description 2
- 231100000029 gastro-duodenal ulcer Toxicity 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000000932 sedative agent Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 230000004873 systolic arterial blood pressure Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 206010065929 Cardiovascular insufficiency Diseases 0.000 description 1
- 206010065390 Inflammatory pain Diseases 0.000 description 1
- 208000007101 Muscle Cramp Diseases 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 208000005392 Spasm Diseases 0.000 description 1
- OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical compound [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 229960003883 furosemide Drugs 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000001631 hypertensive effect Effects 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 230000000793 phophlogistic effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- YCKAGGHNUHZKCL-XQRVVYSFSA-N propan-2-yl (z)-3-aminobut-2-enoate Chemical compound CC(C)OC(=O)\C=C(\C)N YCKAGGHNUHZKCL-XQRVVYSFSA-N 0.000 description 1
- 208000023504 respiratory system disease Diseases 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003826 tablet Substances 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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)
- Indole Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7310202A FR2222086B2 (en:Method) | 1973-03-21 | 1973-03-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2408603A1 true DE2408603A1 (de) | 1974-09-26 |
Family
ID=9116661
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19742408603 Pending DE2408603A1 (de) | 1973-03-21 | 1974-02-22 | Substituierte (5,6,e)oxazinindole, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| DE19742462471 Ceased DE2462471A1 (de) | 1973-03-21 | 1974-02-22 | 2-methyl-3-alkoxycarbonyl-5-hydroxy- indole und verfahren zu ihrer herstellung |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19742462471 Ceased DE2462471A1 (de) | 1973-03-21 | 1974-02-22 | 2-methyl-3-alkoxycarbonyl-5-hydroxy- indole und verfahren zu ihrer herstellung |
Country Status (11)
| Country | Link |
|---|---|
| JP (1) | JPS49126698A (en:Method) |
| BE (1) | BE811263R (en:Method) |
| CA (1) | CA1016546A (en:Method) |
| CH (1) | CH560704A5 (en:Method) |
| DE (2) | DE2408603A1 (en:Method) |
| ES (1) | ES424221A2 (en:Method) |
| FR (1) | FR2222086B2 (en:Method) |
| GB (1) | GB1417381A (en:Method) |
| IT (1) | IT1059819B (en:Method) |
| LU (1) | LU69436A1 (en:Method) |
| NL (1) | NL7403863A (en:Method) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007136300A2 (fr) | 2006-05-23 | 2007-11-29 | Alla Chem, Llc | Indoles substitués et procédé de production et d'utilisation de ceux-ci |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2323221C9 (ru) * | 2006-05-23 | 2010-03-27 | Андрей Александрович Иващенко | ЗАМЕЩЕННЫЕ ЭФИРЫ 1,2,3,7-ТЕТРАГИДРОПИРРОЛО[3,2-f][1,3]БЕНЗОКСАЗИН-5-КАРБОНОВЫХ КИСЛОТ, ФАРМАЦЕВТИЧЕСКАЯ КОМПОЗИЦИЯ, СПОСОБ ИХ ПОЛУЧЕНИЯ (ВАРИАНТЫ) И ПРИМЕНЕНИЯ |
-
1973
- 1973-03-21 FR FR7310202A patent/FR2222086B2/fr not_active Expired
-
1974
- 1974-02-14 GB GB670874A patent/GB1417381A/en not_active Expired
- 1974-02-19 BE BE141119A patent/BE811263R/xx active
- 1974-02-21 LU LU69436A patent/LU69436A1/xx unknown
- 1974-02-22 DE DE19742408603 patent/DE2408603A1/de active Pending
- 1974-02-22 DE DE19742462471 patent/DE2462471A1/de not_active Ceased
- 1974-03-13 ES ES424221A patent/ES424221A2/es not_active Expired
- 1974-03-15 IT IT67788/74A patent/IT1059819B/it active
- 1974-03-18 JP JP49030164A patent/JPS49126698A/ja active Pending
- 1974-03-20 CA CA195,492A patent/CA1016546A/en not_active Expired
- 1974-03-21 NL NL7403863A patent/NL7403863A/xx not_active Application Discontinuation
- 1974-03-21 CH CH394574A patent/CH560704A5/xx not_active IP Right Cessation
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007136300A2 (fr) | 2006-05-23 | 2007-11-29 | Alla Chem, Llc | Indoles substitués et procédé de production et d'utilisation de ceux-ci |
| WO2007136300A3 (fr) * | 2006-05-23 | 2008-02-07 | Alla Chem Llc | Indoles substitués et procédé de production et d'utilisation de ceux-ci |
| EA016633B1 (ru) * | 2006-05-23 | 2012-06-29 | Общество С Ограниченной Ответственностью "Инновационная Фармацевтика" | Замещенные индолы, способ их получения и применения |
| US8329689B2 (en) | 2006-05-23 | 2012-12-11 | Alexandre Vasilievich Ivachtchenko | Substituted indoles and a method for the production and use thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| ES424221A2 (es) | 1976-05-16 |
| FR2222086B2 (en:Method) | 1976-04-09 |
| NL7403863A (en:Method) | 1974-09-24 |
| BE811263R (fr) | 1974-08-19 |
| IT1059819B (it) | 1982-06-21 |
| DE2462471A1 (de) | 1977-05-26 |
| LU69436A1 (en:Method) | 1974-09-25 |
| GB1417381A (en) | 1975-12-10 |
| CH560704A5 (en:Method) | 1975-04-15 |
| FR2222086A2 (en:Method) | 1974-10-18 |
| JPS49126698A (en:Method) | 1974-12-04 |
| CA1016546A (en) | 1977-08-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHW | Rejection |