IE831148L - PYRROLO £3,4-d| £2| BENZAZEPINES - Google Patents
PYRROLO £3,4-d| £2| BENZAZEPINESInfo
- Publication number
- IE831148L IE831148L IE831148A IE114883A IE831148L IE 831148 L IE831148 L IE 831148L IE 831148 A IE831148 A IE 831148A IE 114883 A IE114883 A IE 114883A IE 831148 L IE831148 L IE 831148L
- Authority
- IE
- Ireland
- Prior art keywords
- signifies
- alkyl
- hydrogen
- formula
- hydroxy
- Prior art date
Links
- 150000008038 benzoazepines Chemical class 0.000 title 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 20
- 239000001257 hydrogen Substances 0.000 abstract 20
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 19
- 150000001875 compounds Chemical class 0.000 abstract 14
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 abstract 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 9
- 125000001424 substituent group Chemical group 0.000 abstract 9
- 238000004519 manufacturing process Methods 0.000 abstract 7
- 125000004043 oxo group Chemical group O=* 0.000 abstract 5
- 150000003839 salts Chemical class 0.000 abstract 5
- 150000001204 N-oxides Chemical class 0.000 abstract 4
- 229910052736 halogen Inorganic materials 0.000 abstract 4
- 150000002367 halogens Chemical class 0.000 abstract 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- -1 (C1 -C7 )-alkoxy Chemical group 0.000 abstract 2
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 230000001590 oxidative effect Effects 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 2
- AGOHXMSGPOYHLT-UHFFFAOYSA-N pyrrolo[3,4-d][2]benzazepine Chemical class N1=CC2=CC=CC=C2C2=CN=CC2=C1 AGOHXMSGPOYHLT-UHFFFAOYSA-N 0.000 abstract 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- 150000007942 carboxylates Chemical class 0.000 abstract 1
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 abstract 1
- ACKFDYCQCBEDNU-UHFFFAOYSA-J lead(2+);tetraacetate Chemical compound [Pb+2].CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O ACKFDYCQCBEDNU-UHFFFAOYSA-J 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 150000004965 peroxy acids Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/147—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/30—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with halogen containing compounds, e.g. hypohalogenation
- C07C45/305—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with halogen containing compounds, e.g. hypohalogenation with halogenochromate reagents, e.g. pyridinium chlorochromate
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members 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
-
- 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
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/94—[b, c]- or [b, d]-condensed containing carbocyclic rings other than six-membered
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
1. Claims (for the Contracting States : BE, CH, DE, FR, GB, IT, LI, LU, NL, SE) Pyrrolo[3,4-d][2]benzazepine derivatives of the general formula see diagramm : EP0094668,P27,F1 wherein R1 and R3 signify hydrogen, (C1 -C7 )-alkyl, hydroxy, (C1 -C7 )-alkoxy or the group -OCOR', R' signifies hydrogen (C1 -C6 )-alkyl or phenyl and R2 and R4 signify hydrogen or R1 and R2 and/or R3 and R4 together signify oxo groups, with the proviso that at least one oxo group is present, R signifies hydrogen, (C1 -C7 )-alkyl, hydroxy-(C2 -C7 )-alkyl, amino-(C2 -C7 )-alkyl, mono- or di-(C1 -C7 )-alkylamino-(C2 -C7 )-alkyl or the group -(C1 -C6 )-alkyl-COR**21 , R**21 signifies hydroxy, (C1 -C7 )-alkoxy, amino or mono- or di-(C1 -C7 )-alkylamino, R5 signifies halogen with an atomic number not exceeding 35 or hydrogen and R6 signifies halogen with an atomic number not exceeding 35, with the proviso that R signifies (C1 -C7 )-alkyl or hydrogen when R1 or R3 signifies hydroxy, (C1 -C7 )-alkoxy or -OCOR', the N-oxides and the pharmaceutically acceptable salts thereof. 1. Claims (for the Contracting State AT) A process for the manufacture of pyrrolo[3,4-d][2]benzazepine derivatives of the general formula see diagramm : EP0094668,P29,F2 wherein R1 and R3 signify hydrogen, (C1 -C7 )-alkyl, hydroxy, (C1 -C7 )-alkoxy or the group -OCOR', R' signifies hydrogen, (C1 -C6 )-alkyl or phenyl and R2 and R4 signify hydrogen or R1 and R2 and/or R3 and R4 together signify oxo groups, with the proviso that at least one oxo group is present, R signifies hydrogen, (C1 -C7 )-alkyl, hydroxy-(C2 -C7 )-alkyl, amino-(C2 -C7 )-alkyl, mono- or di-(C1 -C7 )-alkylamino-(C2 -C7 )-alkyl or the group -(C1 -C6 )-alkyl-COR**21 , R**21 signifies hydroxy, (C1 -C7 )-alkoxy, amino or mono- or di-(C1 -C7 )-alkylamino, R5 signifies halogen with an atomic number not exceeding 35 or hydrogen and R6 signifies halogen with an atomic number not exceeding 35, with the proviso that R signifies (C1 -C7 )-alkyl or hydrogen when R1 or R3 signifies hydroxy, (C1 -C7 )-alkoxy or -OCOR', of N-oxides and of pharmaceutically acceptable salts thereof, characterized by a) for the manufacture of compounds of formula I above in which R1 or R3 signifies hydrogen or (C1 -C7 )-alkyl and the remaining symbols have the above significance and of N-oxides thereof, oxidizing a compound of the general formula see diagramm : EP0094668,P30,F1 wherein one of R11 and R31 signifies hydrogen and the other signifies hydrogen or (C1 -C7 )-alkyl and R, R5 and R6 have the above significance, with a peracid, or b) for the manufacture of compounds of formula I above in which R1 or R3 signifies hydroxy and the remaining substituents have the above significance or R1 and R3 and R4 in each case together signify oxo groups and the remaining symbols have the above significance, oxidizing a compound of formula I in which R1 or R3 signifies hydrogen and the remaining substituents have the above significance or a compound of formula II above in which R11 and R31 signify hydrogen with a lead (IV) carboxylate in the presence of a strong acid, or c) for the manufacture of compounds of formula I above in which R1 or R3 signifies acetoxy and the remaining substituents have the above significance, treating a compound of formula I in which R1 or R3 signifies hydrogen and the remaining substituents have the above significance or a compound of formula II above in which R11 and R31 signify hydrogen with lead tetraacetate in acetic acid, or d) for the manufacture of compounds of formula I above in which R1 or R3 signifies -OCOR' and the remaining substituents have the above significance, treating a compound of formula I in which R1 or R3 signifies hydroxy and the remaining substituents have the above significance with a carboxylic acid anhydride in the presence of a base, or e) for the manufacture of compounds of formula I above in which R1 or R3 signifies (C1 -C7 )-alkoxy and the remaining substituents have the above significance, treating a compound of formula I in which R1 or R3 signifies -OCOR' or hydroxy and the remaining substituents have the above significance or a compound of the formula see diagramm : EP0094668,P30,F2 wherein R12 signifies acetoxy and R, R5 and R6 have the above significance, with a (C1 -C7 )-alkanol in the presence of a strong acid, or f) for the manufacture of compounds of formula I above in which R1 or R3 signifies hydrogen or (C1 -C7 )-alkyl and the remaining substituents have the above significance, desoxidizing an N-oxide of the general formula see diagramm : EP0094668,P31,F1 wherein R, R1 , R2 , R3 , R4 , R5 and R6 have the above significance, and, if desired, g) converting a compound of formula I into a pharmaceutically acceptable salt or converting a pharmaceutically acceptable salt of a compound of formula I into another pharmaceutically acceptable salt.
[EP0094668A2]
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US37940082A | 1982-05-18 | 1982-05-18 | |
| US39314282A | 1982-06-28 | 1982-06-28 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE831148L true IE831148L (en) | 1983-11-18 |
| IE55134B1 IE55134B1 (en) | 1990-06-06 |
Family
ID=27008604
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE1148/83A IE55134B1 (en) | 1982-05-18 | 1983-05-17 | Pyrrolo(3,4-d)(2)benzazepine derivatives |
Country Status (9)
| Country | Link |
|---|---|
| EP (1) | EP0094668B1 (en) |
| AU (1) | AU558354B2 (en) |
| CA (1) | CA1202970A (en) |
| DE (1) | DE3372369D1 (en) |
| DK (1) | DK218583A (en) |
| IE (1) | IE55134B1 (en) |
| IL (1) | IL68711A (en) |
| NZ (1) | NZ204242A (en) |
| PH (1) | PH19004A (en) |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL7605526A (en) * | 1976-05-24 | 1977-11-28 | Akzo Nv | NEW TETRACYCLICAL DERIVATIVES. |
| US4354973A (en) * | 1980-08-05 | 1982-10-19 | Hoffmann-La Roche Inc. | Pyrrolo[3,4-d][2]benzazepines |
-
1983
- 1983-05-16 IL IL68711A patent/IL68711A/en unknown
- 1983-05-16 NZ NZ204242A patent/NZ204242A/en unknown
- 1983-05-16 DE DE8383104815T patent/DE3372369D1/en not_active Expired
- 1983-05-16 EP EP83104815A patent/EP0094668B1/en not_active Expired
- 1983-05-16 CA CA000428213A patent/CA1202970A/en not_active Expired
- 1983-05-17 AU AU14605/83A patent/AU558354B2/en not_active Ceased
- 1983-05-17 IE IE1148/83A patent/IE55134B1/en unknown
- 1983-05-17 DK DK218583A patent/DK218583A/en not_active Application Discontinuation
- 1983-05-17 PH PH28914A patent/PH19004A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU558354B2 (en) | 1987-01-29 |
| EP0094668A2 (en) | 1983-11-23 |
| PH19004A (en) | 1985-12-03 |
| CA1202970A (en) | 1986-04-08 |
| IL68711A0 (en) | 1983-09-30 |
| EP0094668A3 (en) | 1985-01-16 |
| AU1460583A (en) | 1983-11-24 |
| DK218583A (en) | 1983-11-19 |
| EP0094668B1 (en) | 1987-07-08 |
| IL68711A (en) | 1986-12-31 |
| NZ204242A (en) | 1986-08-08 |
| IE55134B1 (en) | 1990-06-06 |
| DE3372369D1 (en) | 1987-08-13 |
| DK218583D0 (en) | 1983-05-17 |
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