ES8502441A1 - Novel tetrazine derivatives - Google Patents
Novel tetrazine derivativesInfo
- Publication number
- ES8502441A1 ES8502441A1 ES83524995A ES524995A ES8502441A1 ES 8502441 A1 ES8502441 A1 ES 8502441A1 ES 83524995 A ES83524995 A ES 83524995A ES 524995 A ES524995 A ES 524995A ES 8502441 A1 ES8502441 A1 ES 8502441A1
- Authority
- ES
- Spain
- Prior art keywords
- group
- denotes
- optionally substituted
- substituted phenyl
- alkyl
- 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.)
- Expired
Links
- 150000004905 tetrazines Chemical class 0.000 title abstract 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 9
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 5
- 229910052757 nitrogen Inorganic materials 0.000 abstract 5
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 5
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 abstract 3
- 125000005843 halogen group Chemical group 0.000 abstract 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 2
- 125000000623 heterocyclic group Chemical group 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001301 oxygen Substances 0.000 abstract 2
- 229910052760 oxygen Inorganic materials 0.000 abstract 2
- 125000001424 substituent group Chemical group 0.000 abstract 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 abstract 1
- 239000005864 Sulphur Chemical group 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000000304 alkynyl group Chemical group 0.000 abstract 1
- 230000000118 anti-neoplastic effect Effects 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- -1 cyano, hydroxy Chemical group 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three 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
- C07D231/38—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three 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
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings 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
- C07D233/88—Nitrogen atoms, e.g. allantoin
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings 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
- C07D233/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings 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
- C07D233/91—Nitro radicals
- C07D233/92—Nitro radicals attached in position 4 or 5
-
- 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
- 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
- C07D487/12—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 three hetero rings
- C07D487/14—Ortho-condensed systems
Abstract
Tetrazine derivatives of the general formula < IMAGE > [in which R<1> denotes a (C3-8)-cycloalkyl group or a (C1-4)-alkyl, (C2-6)-alkenyl or (C2-6)-alkynyl group, such an alkyl, alkenyl or alkynyl group being unsubstituted or substituted by 1 to 3 substitutents selected from halogen atoms, (C1-4)-alkoxy, -alkylthio, -alkylsulfinyl and -alkylsulfonyl groups and optionally substituted phenyl groups A1 denotes a nitrogen atom or a group -CR<3>=, in which R<3> denotes hydrogen or a substituent R<4>, where R<4> denotes a halogen atom or a (C1-6)-alkyl or -alkenyl group which can carry up to 3 substituents selected from halogen atoms, optionally substituted phenyl groups, and (C1-3)-alkoxy, -alkylthio and -alkylsulfonyl groups, or R<4> denotes a (C3-8)-cycloalkyl group, a cyano, hydroxy, nitro or optionally substituted phenoxy group or a group -COR<5)<in which R<5> denotes a (C1-4)-alkyl or -alkoxy group, a hydroxy group or an optionally substituted phenyl group) or a (C1-6)-alkanoylamino group, or R<4> denotes a group -S(O)nR<6>, -SO2NR<7>R<8> or -CZ<2>NR<7>R <8> (in which n represents 0, 1 or 2, R<6> denotes a (C1-4)-alkyl or (C2-4)-alkenyl group which can carry an optionally substituted phenyl substituent, a (C3-8)-cycloalkyl group or an optionally substituted phenyl group, where R7 and R8 each denote hydrogen or a (C1-4)-alkyl or (C2-4)-alkenyl group which can carry an optionally substituted phenyl substituent, or a (C3-8)-cycloalkyl group or an optionally substituted phenyl group, or the group -NR<7>R<8> denotes a heterocyclic group and Z<2> denotes an oxygen or sulphur atom) A<2> denotes a nitrogen atom or, if A<1> represents a nitrogen atom, A<2> denotes a nitrogen atom or a group -CR<3>=, in which R<3> is as defined above Z<1> denotes an oxygen or sulphur atom and R<2> denotes a group of the formula -S(O)nR<6>, -SO2NR<7>R<8>, -CSNR<7>R<8>, - CONR<7>R<9> or -CZ<2>NHNO2, in which n, R<6>, R<7>, R<8> and Z<2> are as defined above, and the group -NR<7>R<9> denotes a heterocyclic group, or R<7> is as defined above and R<9> denotes a (C1-4)-alkyl or (C2-4)-alkenyl group which carries an optionally substituted phenyl substituent, or an optionally substituted phenyl group, or if A<1> denotes a nitrogen atom or a group -CR<4>= in which R<4> is as defined above and Z<1> and A<2> are as defined above, or if A<1> denotes a group -CH= and Z<1> denotes a sulphur atom and A<2> is as defined above, R<2> denotes a group of the formula -S(O)nR<6>, -SO2NR<7>R<8>, -CZ<2>NR<7>R<8> or -CZ<2>NHNO2, in which n, R <6 , R<7>, R<8> and Z<2> are as defined above] are novel, therapeutically useful compounds having antineo-plastic activity. Processes for the preparation of the tetrazine derivatives are also described.
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB8223583 | 1982-08-17 | ||
GB8223580 | 1982-08-17 | ||
GB8226169 | 1982-09-14 | ||
GB838306904A GB8306904D0 (en) | 1983-03-14 | 1983-03-14 | Compositions of matter |
Publications (2)
Publication Number | Publication Date |
---|---|
ES524995A0 ES524995A0 (en) | 1985-01-01 |
ES8502441A1 true ES8502441A1 (en) | 1985-01-01 |
Family
ID=27449377
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ES83524995A Expired ES8502441A1 (en) | 1982-08-17 | 1983-08-17 | Novel tetrazine derivatives |
Country Status (18)
Country | Link |
---|---|
AU (1) | AU575782B2 (en) |
BE (1) | BE897548A (en) |
CA (1) | CA1254563A (en) |
CH (1) | CH657855A5 (en) |
DE (1) | DE3329505A1 (en) |
DK (1) | DK374983A (en) |
ES (1) | ES8502441A1 (en) |
FI (1) | FI80273C (en) |
FR (1) | FR2531958B1 (en) |
GR (1) | GR78688B (en) |
HU (1) | HU189321B (en) |
IE (1) | IE55849B1 (en) |
IL (1) | IL69500A (en) |
IT (1) | IT1194375B (en) |
LU (1) | LU84969A1 (en) |
NL (1) | NL8302863A (en) |
NZ (1) | NZ205272A (en) |
SE (1) | SE455198B (en) |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2932305A1 (en) * | 1979-08-09 | 1981-02-26 | Basf Ag | Pyrrolo-, pyrazolo-, imidazo- and thiazolo-tetrazin-4-one derivs. - prepd. from amino-azole cpds. by diazotisation and reaction with isocyanate |
OA07174A (en) * | 1981-08-24 | 1984-04-30 | May & Baker Ltd | New imidazotetrazionones, their preparation and medicines containing them. |
-
1983
- 1983-08-12 FR FR8313246A patent/FR2531958B1/en not_active Expired
- 1983-08-12 GR GR72210A patent/GR78688B/el unknown
- 1983-08-15 HU HU832860A patent/HU189321B/en unknown
- 1983-08-15 AU AU17968/83A patent/AU575782B2/en not_active Ceased
- 1983-08-15 SE SE8304415A patent/SE455198B/en not_active IP Right Cessation
- 1983-08-15 IL IL69500A patent/IL69500A/en unknown
- 1983-08-15 NL NL8302863A patent/NL8302863A/en not_active Application Discontinuation
- 1983-08-15 NZ NZ205272A patent/NZ205272A/en unknown
- 1983-08-15 IE IE1913/83A patent/IE55849B1/en unknown
- 1983-08-15 FI FI832927A patent/FI80273C/en not_active IP Right Cessation
- 1983-08-15 CA CA000434582A patent/CA1254563A/en not_active Expired
- 1983-08-16 LU LU84969A patent/LU84969A1/en unknown
- 1983-08-16 DK DK374983A patent/DK374983A/en not_active Application Discontinuation
- 1983-08-16 IT IT22566/83A patent/IT1194375B/en active
- 1983-08-16 DE DE3329505A patent/DE3329505A1/en not_active Withdrawn
- 1983-08-17 BE BE0/211366A patent/BE897548A/en not_active IP Right Cessation
- 1983-08-17 CH CH4490/83A patent/CH657855A5/en not_active IP Right Cessation
- 1983-08-17 ES ES83524995A patent/ES8502441A1/en not_active Expired
Also Published As
Publication number | Publication date |
---|---|
CH657855A5 (en) | 1986-09-30 |
AU575782B2 (en) | 1988-08-11 |
HU189321B (en) | 1986-06-30 |
ES524995A0 (en) | 1985-01-01 |
FR2531958A1 (en) | 1984-02-24 |
DK374983D0 (en) | 1983-08-16 |
IT8322566A0 (en) | 1983-08-16 |
CA1254563A (en) | 1989-05-23 |
SE455198B (en) | 1988-06-27 |
IL69500A (en) | 1989-01-31 |
GR78688B (en) | 1984-09-27 |
FR2531958B1 (en) | 1986-10-31 |
FI832927A0 (en) | 1983-08-15 |
FI832927A (en) | 1984-02-18 |
FI80273C (en) | 1990-05-10 |
NL8302863A (en) | 1984-03-16 |
DK374983A (en) | 1984-02-18 |
IT1194375B (en) | 1988-09-22 |
DE3329505A1 (en) | 1984-02-23 |
AU1796883A (en) | 1984-02-23 |
IE55849B1 (en) | 1991-01-30 |
SE8304415L (en) | 1984-02-18 |
BE897548A (en) | 1984-02-17 |
SE8304415D0 (en) | 1983-08-15 |
NZ205272A (en) | 1986-12-05 |
FI80273B (en) | 1990-01-31 |
IE831913L (en) | 1984-02-17 |
LU84969A1 (en) | 1984-03-23 |
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