DE2245518A1 - Arylidencyclanone und ihre herstellung und verwendung zur inhibierung der wirkung von androgenen - Google Patents
Arylidencyclanone und ihre herstellung und verwendung zur inhibierung der wirkung von androgenenInfo
- Publication number
- DE2245518A1 DE2245518A1 DE2245518A DE2245518A DE2245518A1 DE 2245518 A1 DE2245518 A1 DE 2245518A1 DE 2245518 A DE2245518 A DE 2245518A DE 2245518 A DE2245518 A DE 2245518A DE 2245518 A1 DE2245518 A1 DE 2245518A1
- Authority
- DE
- Germany
- Prior art keywords
- groups
- chr
- phenyl
- radical
- cyclopentanone
- 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
- 239000003098 androgen Substances 0.000 title claims description 16
- 229940030486 androgens Drugs 0.000 title claims description 11
- 238000004519 manufacturing process Methods 0.000 title description 8
- 230000000694 effects Effects 0.000 title description 6
- -1 naphthyl radical Chemical class 0.000 claims description 60
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 claims description 25
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 20
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims description 18
- 238000002360 preparation method Methods 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
- 125000003282 alkyl amino group Chemical group 0.000 claims description 11
- 150000003997 cyclic ketones Chemical class 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims description 9
- 230000002401 inhibitory effect Effects 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000003277 amino group Chemical group 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 6
- 125000002541 furyl group Chemical group 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 125000005504 styryl group Chemical group 0.000 claims description 6
- 125000001544 thienyl group Chemical group 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- NADUQCROZYTGPH-UHFFFAOYSA-N 2,5-bis[(3,4-dimethoxyphenyl)methylidene]-1-cyclopentanone Chemical compound C1=C(OC)C(OC)=CC=C1C=C(CC1)C(=O)C1=CC1=CC=C(OC)C(OC)=C1 NADUQCROZYTGPH-UHFFFAOYSA-N 0.000 claims description 4
- UJBOOUHRTQVGRU-UHFFFAOYSA-N 3-methylcyclohexan-1-one Chemical compound CC1CCCC(=O)C1 UJBOOUHRTQVGRU-UHFFFAOYSA-N 0.000 claims description 4
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 claims description 4
- WJUFSDZVCOTFON-UHFFFAOYSA-N veratraldehyde Chemical compound COC1=CC=C(C=O)C=C1OC WJUFSDZVCOTFON-UHFFFAOYSA-N 0.000 claims description 4
- AVPYQKSLYISFPO-UHFFFAOYSA-N 4-chlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C=C1 AVPYQKSLYISFPO-UHFFFAOYSA-N 0.000 claims description 3
- OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical compound [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 claims description 3
- 239000003242 anti bacterial agent Substances 0.000 claims description 3
- 239000000051 antiandrogen Substances 0.000 claims description 3
- DHKKONBXGAAFTB-UHFFFAOYSA-N cyclovalone Chemical compound C1=C(O)C(OC)=CC(C=C2C(C(=CC=3C=C(OC)C(O)=CC=3)CCC2)=O)=C1 DHKKONBXGAAFTB-UHFFFAOYSA-N 0.000 claims description 3
- 239000003701 inert diluent Substances 0.000 claims description 3
- 150000003254 radicals Chemical class 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- BGNGWHSBYQYVRX-UHFFFAOYSA-N 4-(dimethylamino)benzaldehyde Chemical compound CN(C)C1=CC=C(C=O)C=C1 BGNGWHSBYQYVRX-UHFFFAOYSA-N 0.000 claims description 2
- BXRFQSNOROATLV-UHFFFAOYSA-N 4-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=C(C=O)C=C1 BXRFQSNOROATLV-UHFFFAOYSA-N 0.000 claims description 2
- YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical class [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 claims description 2
- 230000003115 biocidal effect Effects 0.000 claims description 2
- CGZZMOTZOONQIA-UHFFFAOYSA-N cycloheptanone Chemical group O=C1CCCCCC1 CGZZMOTZOONQIA-UHFFFAOYSA-N 0.000 claims description 2
- CNUDBTRUORMMPA-UHFFFAOYSA-N formylthiophene Chemical compound O=CC1=CC=CS1 CNUDBTRUORMMPA-UHFFFAOYSA-N 0.000 claims description 2
- QNXSIUBBGPHDDE-UHFFFAOYSA-N indan-1-one Chemical compound C1=CC=C2C(=O)CCC2=C1 QNXSIUBBGPHDDE-UHFFFAOYSA-N 0.000 claims description 2
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical group [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 2
- FXLOVSHXALFLKQ-UHFFFAOYSA-N p-tolualdehyde Chemical compound CC1=CC=C(C=O)C=C1 FXLOVSHXALFLKQ-UHFFFAOYSA-N 0.000 claims description 2
- HTSABYAWKQAHBT-UHFFFAOYSA-N trans 3-methylcyclohexanol Natural products CC1CCCC(O)C1 HTSABYAWKQAHBT-UHFFFAOYSA-N 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- GGQPRMNUBBOBJE-PXXPDPNMSA-N (2e,6e)-2,6-dibenzylidene-4-methylcyclohexan-1-one Chemical compound O=C1\C(=C\C=2C=CC=CC=2)CC(C)C\C1=C/C1=CC=CC=C1 GGQPRMNUBBOBJE-PXXPDPNMSA-N 0.000 claims 1
- UOBQDYFTAJKQAL-UHFFFAOYSA-N 2-cyclohexylcyclohexan-1-one Chemical compound O=C1CCCCC1C1CCCCC1 UOBQDYFTAJKQAL-UHFFFAOYSA-N 0.000 claims 1
- 230000001548 androgenic effect Effects 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 51
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 51
- 239000000203 mixture Substances 0.000 description 36
- 238000002844 melting Methods 0.000 description 32
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- MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testostosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 description 29
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 26
- 239000000243 solution Substances 0.000 description 20
- 238000003756 stirring Methods 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- 230000002280 anti-androgenic effect Effects 0.000 description 15
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- 229960003604 testosterone Drugs 0.000 description 14
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 241000700159 Rattus Species 0.000 description 11
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 10
- 239000000126 substance Substances 0.000 description 9
- 229960000583 acetic acid Drugs 0.000 description 8
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 7
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
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- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
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- 238000001953 recrystallisation Methods 0.000 description 4
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- VAPOFMGACKUWCI-UHFFFAOYSA-N 4-(cyclopenten-1-yl)morpholine Chemical compound C1CCC=C1N1CCOCC1 VAPOFMGACKUWCI-UHFFFAOYSA-N 0.000 description 3
- VGVHNLRUAMRIEW-UHFFFAOYSA-N 4-methylcyclohexan-1-one Chemical compound CC1CCC(=O)CC1 VGVHNLRUAMRIEW-UHFFFAOYSA-N 0.000 description 3
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- WUMOJUUCPXEEQL-CSKARUKUSA-N (2e)-2-[(4-chlorophenyl)methylidene]cyclopentan-1-one Chemical compound C1=CC(Cl)=CC=C1\C=C/1C(=O)CCC\1 WUMOJUUCPXEEQL-CSKARUKUSA-N 0.000 description 2
- ITHXOKQJEXLMKO-GXDHUFHOSA-N (2e)-2-benzylidene-3h-inden-1-one Chemical compound C1C2=CC=CC=C2C(=O)\C1=C\C1=CC=CC=C1 ITHXOKQJEXLMKO-GXDHUFHOSA-N 0.000 description 2
- VCDPHYIZVFJQCD-ZRDIBKRKSA-N (2e)-2-benzylidenecyclohexan-1-one Chemical compound O=C1CCCC\C1=C/C1=CC=CC=C1 VCDPHYIZVFJQCD-ZRDIBKRKSA-N 0.000 description 2
- GPXHIYXWGUYGHF-MXWIWYRXSA-N (2e,5e)-2,5-bis[[4-(dimethylamino)phenyl]methylidene]cyclopentan-1-one Chemical compound C1=CC(N(C)C)=CC=C1\C=C(/CC\1)C(=O)C/1=C/C1=CC=C(N(C)C)C=C1 GPXHIYXWGUYGHF-MXWIWYRXSA-N 0.000 description 2
- CDWCNIVDIALVDN-MXWIWYRXSA-N (2e,7e)-2,7-dibenzylidenecycloheptan-1-one Chemical compound O=C1\C(=C\C=2C=CC=CC=2)CCCC\C1=C/C1=CC=CC=C1 CDWCNIVDIALVDN-MXWIWYRXSA-N 0.000 description 2
- FVKZRGBDPHGIQV-UHFFFAOYSA-N 2,5-bis(naphthalen-1-ylmethylidene)cyclopentan-1-one Chemical compound C1=CC=C2C(C=C3C(C(CC3)=CC=3C4=CC=CC=C4C=CC=3)=O)=CC=CC2=C1 FVKZRGBDPHGIQV-UHFFFAOYSA-N 0.000 description 2
- KPFZCKDPBMGECB-UHFFFAOYSA-N 2,5-bis(thiophen-2-ylmethylidene)cyclopentan-1-one Chemical compound O=C1C(=CC=2SC=CC=2)CCC1=CC1=CC=CS1 KPFZCKDPBMGECB-UHFFFAOYSA-N 0.000 description 2
- HOAWLEKLGGIUDF-UHFFFAOYSA-N 2,5-bis[(4-chlorophenyl)methylidene]cyclopentan-1-one Chemical compound C1=CC(Cl)=CC=C1C=C(CC1)C(=O)C1=CC1=CC=C(Cl)C=C1 HOAWLEKLGGIUDF-UHFFFAOYSA-N 0.000 description 2
- DWPJEPVQLUJRMB-UHFFFAOYSA-N 2,5-bis[(4-methoxyphenyl)methylidene]cyclopentan-1-one Chemical compound C1=CC(OC)=CC=C1C=C(CC1)C(=O)C1=CC1=CC=C(OC)C=C1 DWPJEPVQLUJRMB-UHFFFAOYSA-N 0.000 description 2
- WRYUFOKEOTWUFL-UHFFFAOYSA-N 2,5-bis[(4-nitrophenyl)methylidene]cyclopentan-1-one Chemical compound C1=CC([N+](=O)[O-])=CC=C1C=C(CC1)C(=O)C1=CC1=CC=C([N+]([O-])=O)C=C1 WRYUFOKEOTWUFL-UHFFFAOYSA-N 0.000 description 2
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- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/22—Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/45—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by at least one doubly—bound oxygen atom, not being part of a —CHO group
-
- 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
- C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
-
- 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
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
- C07C45/74—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups combined with dehydration
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/657—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings
- C07C49/683—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings having unsaturation outside the aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/687—Unsaturated compounds containing a keto groups being part of a ring containing halogen
- C07C49/697—Unsaturated compounds containing a keto groups being part of a ring containing halogen containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/753—Unsaturated compounds containing a keto groups being part of a ring containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/753—Unsaturated compounds containing a keto groups being part of a ring containing ether groups, groups, groups, or groups
- C07C49/755—Unsaturated compounds containing a keto groups being part of a ring containing ether groups, groups, groups, or groups a keto group being part of a condensed ring system with two or three rings, at least one ring being a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/40—Radicals substituted by oxygen atoms
- C07D307/46—Doubly bound oxygen atoms, or two oxygen atoms singly bound to the same carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
- C07D317/54—Radicals substituted by oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Furan Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US18212371A | 1971-09-20 | 1971-09-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2245518A1 true DE2245518A1 (de) | 1973-04-26 |
Family
ID=22667147
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2245518A Pending DE2245518A1 (de) | 1971-09-20 | 1972-09-15 | Arylidencyclanone und ihre herstellung und verwendung zur inhibierung der wirkung von androgenen |
Country Status (15)
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2833880A1 (de) * | 1977-08-04 | 1979-02-22 | Unicler Sa | Alpha -benzyliden-cycloalkanderivate, verfahren zu ihrer herstellung und sie enthaltende arzneimittel |
| US4354976A (en) * | 1979-12-19 | 1982-10-19 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Process for the preparation of azidobenzal compounds |
| FR2641277A1 (fr) * | 1988-12-29 | 1990-07-06 | Rhone Poulenc Agrochimie | Azolylmethylcyclopentane ou cyclopentene benzolidene et utilisation comme fongicide |
| EP0378953A1 (fr) * | 1988-12-29 | 1990-07-25 | Rhone-Poulenc Agrochimie | Benzylidène azolylméthylecycloalcane et utilisation comme fongicide |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4857029A (enrdf_load_stackoverflow) * | 1971-09-22 | 1973-08-10 | ||
| JPS493029A (enrdf_load_stackoverflow) * | 1972-04-27 | 1974-01-11 | ||
| JPS5074038A (enrdf_load_stackoverflow) * | 1973-11-07 | 1975-06-18 | ||
| FR2649101B1 (fr) * | 1989-06-30 | 1994-10-28 | Rhone Poulenc Agrochimie | Azolylmethylcyclohexane benzilidene et utilisation comme fongicide |
| JPH10273467A (ja) * | 1997-01-29 | 1998-10-13 | Snow Brand Milk Prod Co Ltd | 新規テトラロン又はベンゾピラノン誘導体及びその製造方法 |
| US6162810A (en) * | 1997-11-17 | 2000-12-19 | The Regents Of The University Of California | Inadone and tetralone compounds for inhibiting cell proliferation |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1160689A (fr) * | 1953-04-13 | 1958-07-24 | Anton Von Waldheim Chemisch Ph | Procédé de préparation de divanillydène-cyclohexanone |
| FR64M (enrdf_load_stackoverflow) * | 1960-07-22 | 1961-01-09 | ||
| FR1867M (fr) * | 1962-04-12 | 1963-06-17 | Egema | Composition nouvelle destinée notamment au traitement de la cholestérolémie. |
| FR1414456A (fr) * | 1964-11-19 | 1965-10-15 | Eastman Kodak Co | Procédé de préparation des 2-alcoylbutanones et produits obtenus par la mise en oevre de ce procédé |
-
0
- BE BE788991D patent/BE788991A/xx unknown
-
1972
- 1972-08-28 ZA ZA725886A patent/ZA725886B/xx unknown
- 1972-08-28 IL IL40220A patent/IL40220A/en unknown
- 1972-08-30 CA CA150,548A patent/CA986015A/en not_active Expired
- 1972-08-31 AU AU46183/72A patent/AU463813B2/en not_active Expired
- 1972-09-01 IE IE1189/72A patent/IE36663B1/xx unknown
- 1972-09-07 PH PH13872A patent/PH10556A/en unknown
- 1972-09-15 DE DE2245518A patent/DE2245518A1/de active Pending
- 1972-09-18 PL PL1972157806A patent/PL85198B1/pl unknown
- 1972-09-19 ES ES406846A patent/ES406846A1/es not_active Expired
- 1972-09-19 GB GB4337572A patent/GB1394717A/en not_active Expired
- 1972-09-20 NL NL7212741A patent/NL7212741A/xx not_active Application Discontinuation
- 1972-09-20 DD DD165766A patent/DD103811A5/xx unknown
- 1972-09-20 FR FR7233325A patent/FR2154536B1/fr not_active Expired
- 1972-09-20 JP JP47093762A patent/JPS4836155A/ja active Pending
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2833880A1 (de) * | 1977-08-04 | 1979-02-22 | Unicler Sa | Alpha -benzyliden-cycloalkanderivate, verfahren zu ihrer herstellung und sie enthaltende arzneimittel |
| US4354976A (en) * | 1979-12-19 | 1982-10-19 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Process for the preparation of azidobenzal compounds |
| FR2641277A1 (fr) * | 1988-12-29 | 1990-07-06 | Rhone Poulenc Agrochimie | Azolylmethylcyclopentane ou cyclopentene benzolidene et utilisation comme fongicide |
| EP0378953A1 (fr) * | 1988-12-29 | 1990-07-25 | Rhone-Poulenc Agrochimie | Benzylidène azolylméthylecycloalcane et utilisation comme fongicide |
| AU637779B2 (en) * | 1988-12-29 | 1993-06-10 | Basf Agro B.V., Arnhem (Nl)- Wadenswil Branch | (benzylidene)-azolylmethylcycloalkane or-alkene and use as fungicide |
| US5639918A (en) * | 1988-12-29 | 1997-06-17 | Rhone-Poulenc Agrochimie | Intermediate compounds useful in the preparation of fungicidal compositions containing (benzylidene)-azolylmethyclycloalkane |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1394717A (en) | 1975-05-21 |
| DD103811A5 (enrdf_load_stackoverflow) | 1974-02-12 |
| AU463813B2 (en) | 1975-08-07 |
| BE788991A (fr) | 1973-03-19 |
| FR2154536B1 (enrdf_load_stackoverflow) | 1976-07-02 |
| CA986015A (en) | 1976-03-23 |
| ES406846A1 (es) | 1976-05-01 |
| PL85198B1 (enrdf_load_stackoverflow) | 1976-04-30 |
| JPS4836155A (enrdf_load_stackoverflow) | 1973-05-28 |
| AU4618372A (en) | 1974-03-07 |
| NL7212741A (enrdf_load_stackoverflow) | 1973-03-22 |
| IL40220A0 (en) | 1972-10-29 |
| PH10556A (en) | 1977-06-08 |
| IE36663B1 (en) | 1977-01-19 |
| ZA725886B (en) | 1974-04-24 |
| IL40220A (en) | 1976-07-30 |
| IE36663L (en) | 1973-03-20 |
| FR2154536A1 (enrdf_load_stackoverflow) | 1973-05-11 |
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| OHA | Expiration of time for request for examination |