DE2647906C2 - Aroylphenylindene und Aroylphenylnaphthaline und -hydronaphthaline sowie Verfahren zu ihrer Herstellung - Google Patents
Aroylphenylindene und Aroylphenylnaphthaline und -hydronaphthaline sowie Verfahren zu ihrer HerstellungInfo
- Publication number
- DE2647906C2 DE2647906C2 DE2647906A DE2647906A DE2647906C2 DE 2647906 C2 DE2647906 C2 DE 2647906C2 DE 2647906 A DE2647906 A DE 2647906A DE 2647906 A DE2647906 A DE 2647906A DE 2647906 C2 DE2647906 C2 DE 2647906C2
- Authority
- DE
- Germany
- Prior art keywords
- phenyl
- compounds
- mixture
- formula
- compound
- 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
- 238000002360 preparation method Methods 0.000 title description 10
- 238000000034 method Methods 0.000 title description 8
- 239000001257 hydrogen Substances 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 description 60
- 239000000203 mixture Substances 0.000 description 35
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 30
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 125000001424 substituent group Chemical group 0.000 description 20
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- 239000000243 solution Substances 0.000 description 15
- 230000035558 fertility Effects 0.000 description 14
- 230000002401 inhibitory effect Effects 0.000 description 13
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 12
- -1 C] -C 5 -AlkOXy Chemical compound 0.000 description 11
- 241001465754 Metazoa Species 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 238000004458 analytical method Methods 0.000 description 8
- 239000000155 melt Substances 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 150000002431 hydrogen Chemical class 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 241000700159 Rattus Species 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 6
- 239000010410 layer Substances 0.000 description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 6
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 241000282421 Canidae Species 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 5
- ANRQGKOBLBYXFM-UHFFFAOYSA-M phenylmagnesium bromide Chemical compound Br[Mg]C1=CC=CC=C1 ANRQGKOBLBYXFM-UHFFFAOYSA-M 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 241000271566 Aves Species 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 235000019198 oils Nutrition 0.000 description 4
- 230000035935 pregnancy Effects 0.000 description 4
- 239000002002 slurry Substances 0.000 description 4
- QJDUDPQVDAASMV-UHFFFAOYSA-M sodium;ethanethiolate Chemical compound [Na+].CC[S-] QJDUDPQVDAASMV-UHFFFAOYSA-M 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000001819 mass spectrum Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- 229910052725 zinc Inorganic materials 0.000 description 3
- RJQTVZQAFBFYGW-UHFFFAOYSA-N (4-hydroxyphenyl)-(6-hydroxy-3-phenyl-1h-inden-2-yl)methanone Chemical compound C1=CC(O)=CC=C1C(=O)C1=C(C=2C=CC=CC=2)C2=CC=C(O)C=C2C1 RJQTVZQAFBFYGW-UHFFFAOYSA-N 0.000 description 2
- JFPAZHMKWHOGKS-UHFFFAOYSA-N (4-methoxyphenyl)-(6-methoxy-1-phenyl-3,4-dihydronaphthalen-2-yl)methanone Chemical compound C1=CC(OC)=CC=C1C(=O)C(CCC1=CC(OC)=CC=C11)=C1C1=CC=CC=C1 JFPAZHMKWHOGKS-UHFFFAOYSA-N 0.000 description 2
- PANZFQYXPMCHFD-UHFFFAOYSA-N 2,3-diphenyl-1h-indene Chemical class C12=CC=CC=C2CC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 PANZFQYXPMCHFD-UHFFFAOYSA-N 0.000 description 2
- FRIGLBWVTJAEHM-UHFFFAOYSA-N 3,4-diphenyl-1,2-dihydronaphthalene Chemical class C1CC2=CC=CC=C2C(C=2C=CC=CC=2)=C1C1=CC=CC=C1 FRIGLBWVTJAEHM-UHFFFAOYSA-N 0.000 description 2
- 125000001999 4-Methoxybenzoyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C(*)=O 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 229910015900 BF3 Inorganic materials 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000013329 compounding Methods 0.000 description 2
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 244000144993 groups of animals Species 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- BNZYBNYNPXKWCM-UHFFFAOYSA-N phenyl 4-methoxybenzoate Chemical compound C1=CC(OC)=CC=C1C(=O)OC1=CC=CC=C1 BNZYBNYNPXKWCM-UHFFFAOYSA-N 0.000 description 2
- 229920000137 polyphosphoric acid Polymers 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 150000003431 steroids Chemical class 0.000 description 2
- 239000003981 vehicle Substances 0.000 description 2
- RURCGKORRUHWEE-UHFFFAOYSA-N (1-phenyl-3,4-dihydronaphthalen-2-yl)-(4-propan-2-yloxyphenyl)methanone Chemical compound C1=CC(OC(C)C)=CC=C1C(=O)C(CCC1=CC=CC=C11)=C1C1=CC=CC=C1 RURCGKORRUHWEE-UHFFFAOYSA-N 0.000 description 1
- WIHHIHONJKPWLR-UHFFFAOYSA-N (1-phenylnaphthalen-2-yl)-(4-propan-2-yloxyphenyl)methanone Chemical compound C1=CC(OC(C)C)=CC=C1C(=O)C1=CC=C(C=CC=C2)C2=C1C1=CC=CC=C1 WIHHIHONJKPWLR-UHFFFAOYSA-N 0.000 description 1
- SNHTULUCLCJKDC-UHFFFAOYSA-N (2-methoxyphenyl)-(1-phenyl-3,4-dihydronaphthalen-2-yl)methanone Chemical compound COC1=CC=CC=C1C(=O)C(CCC1=CC=CC=C11)=C1C1=CC=CC=C1 SNHTULUCLCJKDC-UHFFFAOYSA-N 0.000 description 1
- OLWWVXSVAHNATM-UHFFFAOYSA-N (2-methoxyphenyl)-(1-phenylnaphthalen-2-yl)methanone Chemical compound COC1=CC=CC=C1C(=O)C1=CC=C(C=CC=C2)C2=C1C1=CC=CC=C1 OLWWVXSVAHNATM-UHFFFAOYSA-N 0.000 description 1
- FHYTXIMJVHAGEX-UHFFFAOYSA-N (2-methoxyphenyl)-(3-phenyl-1h-inden-2-yl)methanone Chemical compound COC1=CC=CC=C1C(=O)C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C1 FHYTXIMJVHAGEX-UHFFFAOYSA-N 0.000 description 1
- REOPUHOCQYANCA-UHFFFAOYSA-N (3-cyclopentyloxyphenyl)-(3-phenyl-1h-inden-2-yl)methanone Chemical compound C=1C=CC(OC2CCCC2)=CC=1C(=O)C(CC1=CC=CC=C11)=C1C1=CC=CC=C1 REOPUHOCQYANCA-UHFFFAOYSA-N 0.000 description 1
- PSVSUELSJTVLSA-UHFFFAOYSA-N (3-cyclopentyloxyphenyl)-(6-hydroxy-1-phenyl-3,4-dihydronaphthalen-2-yl)methanone Chemical compound C1CC2=CC(O)=CC=C2C(C=2C=CC=CC=2)=C1C(=O)C(C=1)=CC=CC=1OC1CCCC1 PSVSUELSJTVLSA-UHFFFAOYSA-N 0.000 description 1
- XSZZMVUWLLSFOJ-UHFFFAOYSA-N (3-ethoxyphenyl)-(1-phenyl-3,4-dihydronaphthalen-2-yl)methanone Chemical compound CCOC1=CC=CC(C(=O)C=2CCC3=CC=CC=C3C=2C=2C=CC=CC=2)=C1 XSZZMVUWLLSFOJ-UHFFFAOYSA-N 0.000 description 1
- YBTWSFJLDVXDJH-UHFFFAOYSA-N (3-ethoxyphenyl)-(3-phenyl-1h-inden-2-yl)methanone Chemical compound CCOC1=CC=CC(C(=O)C=2CC3=CC=CC=C3C=2C=2C=CC=CC=2)=C1 YBTWSFJLDVXDJH-UHFFFAOYSA-N 0.000 description 1
- RITLIYJHAUOYNX-UHFFFAOYSA-N (3-hydroxyphenyl)-(1-phenyl-3,4-dihydronaphthalen-2-yl)methanone Chemical compound OC1=CC=CC(C(=O)C=2CCC3=CC=CC=C3C=2C=2C=CC=CC=2)=C1 RITLIYJHAUOYNX-UHFFFAOYSA-N 0.000 description 1
- ZTIZJSNCARSUAH-UHFFFAOYSA-N (3-hydroxyphenyl)-(1-phenylnaphthalen-2-yl)methanone Chemical compound OC1=CC=CC(C(=O)C=2C(=C3C=CC=CC3=CC=2)C=2C=CC=CC=2)=C1 ZTIZJSNCARSUAH-UHFFFAOYSA-N 0.000 description 1
- AHKIAFDCGVTACB-UHFFFAOYSA-N (3-hydroxyphenyl)-(3-phenyl-1h-inden-2-yl)methanone Chemical compound OC1=CC=CC(C(=O)C=2CC3=CC=CC=C3C=2C=2C=CC=CC=2)=C1 AHKIAFDCGVTACB-UHFFFAOYSA-N 0.000 description 1
- FODJGTKUNGRYAH-UHFFFAOYSA-N (3-phenyl-1h-inden-2-yl)-(4-propan-2-yloxyphenyl)methanone Chemical compound C1=CC(OC(C)C)=CC=C1C(=O)C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C1 FODJGTKUNGRYAH-UHFFFAOYSA-N 0.000 description 1
- WYJJCYGHOQCWRK-UHFFFAOYSA-N (4-cyclohexyloxyphenyl)-(1-phenyl-3,4-dihydronaphthalen-2-yl)methanone Chemical compound C=1C=C(OC2CCCCC2)C=CC=1C(=O)C(CCC1=CC=CC=C11)=C1C1=CC=CC=C1 WYJJCYGHOQCWRK-UHFFFAOYSA-N 0.000 description 1
- SLRFJKITKWTLMQ-UHFFFAOYSA-N (4-cyclohexyloxyphenyl)-(1-phenylnaphthalen-2-yl)methanone Chemical compound C=1C=C2C=CC=CC2=C(C=2C=CC=CC=2)C=1C(=O)C(C=C1)=CC=C1OC1CCCCC1 SLRFJKITKWTLMQ-UHFFFAOYSA-N 0.000 description 1
- MCZJVMJFZYWMLN-UHFFFAOYSA-N (4-cyclohexyloxyphenyl)-(3-phenyl-1h-inden-2-yl)methanone Chemical compound C=1C=C(OC2CCCCC2)C=CC=1C(=O)C(CC1=CC=CC=C11)=C1C1=CC=CC=C1 MCZJVMJFZYWMLN-UHFFFAOYSA-N 0.000 description 1
- VBKXLXCGRUVRQO-UHFFFAOYSA-N (4-hydroxyphenyl)-(6-hydroxy-1-phenyl-3,4-dihydronaphthalen-2-yl)methanone Chemical compound C1=CC(O)=CC=C1C(=O)C(CCC1=CC(O)=CC=C11)=C1C1=CC=CC=C1 VBKXLXCGRUVRQO-UHFFFAOYSA-N 0.000 description 1
- CLPOERWSGYHPPI-UHFFFAOYSA-N (4-hydroxyphenyl)-(6-hydroxy-1-phenylnaphthalen-2-yl)methanone Chemical compound C1=CC(O)=CC=C1C(=O)C1=CC=C(C=C(O)C=C2)C2=C1C1=CC=CC=C1 CLPOERWSGYHPPI-UHFFFAOYSA-N 0.000 description 1
- VFBVZFWBELVADP-UHFFFAOYSA-N (4-methoxyphenyl)-(3-phenyl-1h-inden-2-yl)methanone Chemical compound C1=CC(OC)=CC=C1C(=O)C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C1 VFBVZFWBELVADP-UHFFFAOYSA-N 0.000 description 1
- HKFKOVAPQJBBPD-UHFFFAOYSA-N (4-methoxyphenyl)-(6-methoxy-1-phenylnaphthalen-2-yl)methanone Chemical compound C1=CC(OC)=CC=C1C(=O)C1=CC=C(C=C(OC)C=C2)C2=C1C1=CC=CC=C1 HKFKOVAPQJBBPD-UHFFFAOYSA-N 0.000 description 1
- CVFWKMJYJPBDPV-UHFFFAOYSA-N (4-methoxyphenyl)-(6-methoxy-3-phenyl-1h-inden-2-yl)methanone Chemical compound C1=CC(OC)=CC=C1C(=O)C1=C(C=2C=CC=CC=2)C2=CC=C(OC)C=C2C1 CVFWKMJYJPBDPV-UHFFFAOYSA-N 0.000 description 1
- RLWYEULVDILHNX-UHFFFAOYSA-N (4-pentoxyphenyl)-(1-phenylnaphthalen-2-yl)methanone Chemical compound C1=CC(OCCCCC)=CC=C1C(=O)C1=CC=C(C=CC=C2)C2=C1C1=CC=CC=C1 RLWYEULVDILHNX-UHFFFAOYSA-N 0.000 description 1
- PMLGJZYJWQYIMX-UHFFFAOYSA-N (4-pentoxyphenyl)-(3-phenyl-1h-inden-2-yl)methanone Chemical compound C1=CC(OCCCCC)=CC=C1C(=O)C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C1 PMLGJZYJWQYIMX-UHFFFAOYSA-N 0.000 description 1
- KJSJWEJHHJOEFF-UHFFFAOYSA-N (6-cyclohexyloxy-1-phenyl-3,4-dihydronaphthalen-2-yl)-(4-pentoxyphenyl)methanone Chemical compound C1=CC(OCCCCC)=CC=C1C(=O)C(CCC1=CC(OC2CCCCC2)=CC=C11)=C1C1=CC=CC=C1 KJSJWEJHHJOEFF-UHFFFAOYSA-N 0.000 description 1
- KSJBPNPTNZZBSU-UHFFFAOYSA-N (6-cyclohexyloxy-3-phenyl-1h-inden-2-yl)-(4-pentoxyphenyl)methanone Chemical compound C1=CC(OCCCCC)=CC=C1C(=O)C(CC1=C2)=C(C=3C=CC=CC=3)C1=CC=C2OC1CCCCC1 KSJBPNPTNZZBSU-UHFFFAOYSA-N 0.000 description 1
- XTZLKBJJTZMSIG-UHFFFAOYSA-N (6-ethoxy-1-phenylnaphthalen-2-yl)-(4-propan-2-yloxyphenyl)methanone Chemical compound C=1C=C(OC(C)C)C=CC=1C(=O)C=1C=CC2=CC(OCC)=CC=C2C=1C1=CC=CC=C1 XTZLKBJJTZMSIG-UHFFFAOYSA-N 0.000 description 1
- YXAOGJDFBPUECR-UHFFFAOYSA-N (6-ethoxy-1-phenylnaphthalen-2-yl)-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)C=1C=CC2=CC(OCC)=CC=C2C=1C1=CC=CC=C1 YXAOGJDFBPUECR-UHFFFAOYSA-N 0.000 description 1
- FNJZMKYWKLEHQI-UHFFFAOYSA-N (6-hydroxy-1-phenyl-3,4-dihydronaphthalen-2-yl)-phenylmethanone Chemical compound C1CC2=CC(O)=CC=C2C(C=2C=CC=CC=2)=C1C(=O)C1=CC=CC=C1 FNJZMKYWKLEHQI-UHFFFAOYSA-N 0.000 description 1
- CCHGMNUKXBEJRL-UHFFFAOYSA-N (6-hydroxy-3-phenyl-1h-inden-2-yl)-phenylmethanone Chemical compound C1C2=CC(O)=CC=C2C(C=2C=CC=CC=2)=C1C(=O)C1=CC=CC=C1 CCHGMNUKXBEJRL-UHFFFAOYSA-N 0.000 description 1
- MIUCFGHHWPEKKI-UHFFFAOYSA-N (6-methoxy-3-phenyl-1h-inden-2-yl)-phenylmethanone Chemical compound C1C2=CC(OC)=CC=C2C(C=2C=CC=CC=2)=C1C(=O)C1=CC=CC=C1 MIUCFGHHWPEKKI-UHFFFAOYSA-N 0.000 description 1
- KCYISNRBBKQKTG-UHFFFAOYSA-N (6-pentoxy-3-phenyl-1h-inden-2-yl)-phenylmethanone Chemical compound C1C2=CC(OCCCCC)=CC=C2C(C=2C=CC=CC=2)=C1C(=O)C1=CC=CC=C1 KCYISNRBBKQKTG-UHFFFAOYSA-N 0.000 description 1
- KEIFWROAQVVDBN-UHFFFAOYSA-N 1,2-dihydronaphthalene Chemical group C1=CC=C2C=CCCC2=C1 KEIFWROAQVVDBN-UHFFFAOYSA-N 0.000 description 1
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical class C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 1
- SJGKYVCZSNGHPC-UHFFFAOYSA-N 2-(3-methoxyphenyl)propanoic acid Chemical compound COC1=CC=CC(C(C)C(O)=O)=C1 SJGKYVCZSNGHPC-UHFFFAOYSA-N 0.000 description 1
- MNALUTYMBUBKNX-UHFFFAOYSA-N 6-methoxy-3,4-dihydro-2h-naphthalen-1-one Chemical compound O=C1CCCC2=CC(OC)=CC=C21 MNALUTYMBUBKNX-UHFFFAOYSA-N 0.000 description 1
- QTUANRNBNIECOH-UHFFFAOYSA-N 7,8-dihydronaphthalen-2-ol Chemical class C1=CCCC2=CC(O)=CC=C21 QTUANRNBNIECOH-UHFFFAOYSA-N 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 241000272201 Columbiformes Species 0.000 description 1
- 206010010356 Congenital anomaly Diseases 0.000 description 1
- 206010055690 Foetal death Diseases 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 241000283984 Rodentia Species 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 241000287182 Sturnidae Species 0.000 description 1
- OIJNOWSBXBVNPZ-UHFFFAOYSA-N [3-[(2-methylpropan-2-yl)oxy]phenyl]-(1-phenyl-6-propoxy-3,4-dihydronaphthalen-2-yl)methanone Chemical compound C1CC2=CC(OCCC)=CC=C2C(C=2C=CC=CC=2)=C1C(=O)C1=CC=CC(OC(C)(C)C)=C1 OIJNOWSBXBVNPZ-UHFFFAOYSA-N 0.000 description 1
- LUYDNDCRAYDFPI-UHFFFAOYSA-N [3-[(2-methylpropan-2-yl)oxy]phenyl]-(1-phenylnaphthalen-2-yl)methanone Chemical compound CC(C)(C)OC1=CC=CC(C(=O)C=2C(=C3C=CC=CC3=CC=2)C=2C=CC=CC=2)=C1 LUYDNDCRAYDFPI-UHFFFAOYSA-N 0.000 description 1
- KMYRQKRMYZWBSA-UHFFFAOYSA-N [3-[(2-methylpropan-2-yl)oxy]phenyl]-(3-phenyl-1h-inden-2-yl)methanone Chemical compound CC(C)(C)OC1=CC=CC(C(=O)C=2CC3=CC=CC=C3C=2C=2C=CC=CC=2)=C1 KMYRQKRMYZWBSA-UHFFFAOYSA-N 0.000 description 1
- OHOPXAUVAFAKGY-UHFFFAOYSA-N [3-[(2-methylpropan-2-yl)oxy]phenyl]-(3-phenyl-6-propoxy-1h-inden-2-yl)methanone Chemical compound C1C2=CC(OCCC)=CC=C2C(C=2C=CC=CC=2)=C1C(=O)C1=CC=CC(OC(C)(C)C)=C1 OHOPXAUVAFAKGY-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000003509 anti-fertility effect Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000005667 attractant Substances 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 229940124558 contraceptive agent Drugs 0.000 description 1
- 239000003433 contraceptive agent Substances 0.000 description 1
- 239000002285 corn oil Substances 0.000 description 1
- 235000005687 corn oil Nutrition 0.000 description 1
- 125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 description 1
- 125000001887 cyclopentyloxy group Chemical group C1(CCCC1)O* 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 238000001212 derivatisation Methods 0.000 description 1
- 125000005594 diketone group Chemical group 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000002024 ethyl acetate extract Substances 0.000 description 1
- 210000003754 fetus Anatomy 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 150000002469 indenes Chemical class 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- GWWKBLFPPUSKRQ-UHFFFAOYSA-N phenyl-(3-phenyl-6-propan-2-yloxy-1h-inden-2-yl)methanone Chemical compound C1C2=CC(OC(C)C)=CC=C2C(C=2C=CC=CC=2)=C1C(=O)C1=CC=CC=C1 GWWKBLFPPUSKRQ-UHFFFAOYSA-N 0.000 description 1
- UXCDUFKZSUBXGM-UHFFFAOYSA-N phosphoric tribromide Chemical compound BrP(Br)(Br)=O UXCDUFKZSUBXGM-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- 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
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/46—Friedel-Crafts reactions
-
- 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
- C07C45/65—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 splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups
-
- 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
- C07C45/673—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 change of size of the carbon skeleton
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/625,992 US4017546A (en) | 1975-10-28 | 1975-10-28 | Novel antifertility agents |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2647906A1 DE2647906A1 (de) | 1977-05-05 |
| DE2647906C2 true DE2647906C2 (de) | 1985-01-31 |
Family
ID=24508497
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2647906A Expired DE2647906C2 (de) | 1975-10-28 | 1976-10-22 | Aroylphenylindene und Aroylphenylnaphthaline und -hydronaphthaline sowie Verfahren zu ihrer Herstellung |
Country Status (31)
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4323707A (en) * | 1975-10-28 | 1982-04-06 | Eli Lilly And Company | Antifertility compounds |
| US4017546A (en) * | 1975-10-28 | 1977-04-12 | Eli Lilly And Company | Novel antifertility agents |
| US4230862A (en) * | 1975-10-28 | 1980-10-28 | Eli Lilly And Company | Antifertility compounds |
| US4400543A (en) * | 1975-10-28 | 1983-08-23 | Eli Lilly And Company | 3-Phenyl-4-benzoyl-1,2-dihydronaphthalenes |
| US5552401A (en) * | 1995-02-28 | 1996-09-03 | Eli Lilly And Company | 2-benzyl-3-arylbenzothiophenes |
| US6107346A (en) * | 1997-08-11 | 2000-08-22 | Eli Lilly And Company | Methods for treating hyperlipidemia |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2551316A (en) * | 1948-02-20 | 1951-05-01 | Searle & Co | 9-aminoalkyl 9-alkanoyl 9, 10 dihydroanthracenes |
| US3274213A (en) * | 1961-09-05 | 1966-09-20 | Upjohn Co | Alkoxy-substituted 2-phenyl-1-(tertiary-aminoalkoxy)phenyl-3, 4-dihydronaphthalenes |
| US3396169A (en) * | 1966-10-26 | 1968-08-06 | Upjohn Co | Substituted 2-phenyl-1-(tertiary-aminoalkoxy) phenyl-3, 4-dihydronaphthalenes |
| US3862232A (en) * | 1963-07-03 | 1975-01-21 | Upjohn Co | 1-(p-hydroxyphenyl)-2-phenyl-6-(2-diethylaminoethoxy)-3,4-dihydronaphthalene and the salts thereof |
| US3293263A (en) * | 1963-12-09 | 1966-12-20 | Upjohn Co | Diphenylbenzocycloalkenes |
| US3320271A (en) * | 1964-06-01 | 1967-05-16 | Upjohn Co | 1, 2-diphenyl-3, 4-dihydronaphthalenes and 2, 3-diphenylindenes |
| US3519675A (en) * | 1964-06-01 | 1970-07-07 | Upjohn Co | 1,2-diphenyl-3,4-dihydronaphthalenes and 2,3-diphenylindenes |
| US3483293A (en) * | 1967-12-15 | 1969-12-09 | Upjohn Co | Method for controlling birds and rodents |
| US4017546A (en) * | 1975-10-28 | 1977-04-12 | Eli Lilly And Company | Novel antifertility agents |
-
1975
- 1975-10-28 US US05/625,992 patent/US4017546A/en not_active Expired - Lifetime
-
1976
- 1976-09-02 AU AU17407/76A patent/AU503883B2/en not_active Expired
- 1976-09-05 IL IL50414A patent/IL50414A/xx unknown
- 1976-10-20 JP JP51126786A patent/JPS5253844A/ja active Granted
- 1976-10-20 MX MX764987U patent/MX4320E/es unknown
- 1976-10-21 NZ NZ182426A patent/NZ182426A/xx unknown
- 1976-10-21 CA CA263,843A patent/CA1064926A/en not_active Expired
- 1976-10-22 PH PH19041A patent/PH13486A/en unknown
- 1976-10-22 DE DE2647906A patent/DE2647906C2/de not_active Expired
- 1976-10-22 HU HU76EI712A patent/HU176092B/hu unknown
- 1976-10-25 PT PT65754A patent/PT65754B/pt unknown
- 1976-10-25 GR GR52002A patent/GR61239B/el unknown
- 1976-10-25 GB GB44176/76A patent/GB1562806A/en not_active Expired
- 1976-10-26 RO RO7688225A patent/RO70754A/ro unknown
- 1976-10-26 SU SU762414100A patent/SU654164A3/ru active
- 1976-10-26 ES ES452736A patent/ES452736A1/es not_active Expired
- 1976-10-27 YU YU02621/76A patent/YU262176A/xx unknown
- 1976-10-27 SE SE7611952A patent/SE431086B/xx not_active IP Right Cessation
- 1976-10-27 ZA ZA00766441A patent/ZA766441B/xx unknown
- 1976-10-27 DK DK484676A patent/DK484676A/da not_active Application Discontinuation
- 1976-10-27 CH CH1355276A patent/CH624375A5/de not_active IP Right Cessation
- 1976-10-27 IE IE2373/76A patent/IE43642B1/en unknown
- 1976-10-28 NL NL7611973A patent/NL7611973A/xx not_active Application Discontinuation
- 1976-10-28 BG BG034553A patent/BG27556A3/xx unknown
- 1976-10-28 AR AR265275A patent/AR221031A1/es active
- 1976-10-28 AT AT800676A patent/AT347443B/de not_active IP Right Cessation
- 1976-10-28 DD DD195509A patent/DD127462A5/xx unknown
- 1976-10-28 FR FR7632512A patent/FR2329265A1/fr active Granted
- 1976-10-28 PL PL1976193327A patent/PL106987B1/pl unknown
- 1976-10-28 CS CS766972A patent/CS234003B2/cs unknown
- 1976-10-28 BE BE1007723A patent/BE847717A/xx not_active IP Right Cessation
- 1976-11-24 US US05/744,488 patent/US4075223A/en not_active Expired - Lifetime
-
1979
- 1979-09-17 PH PH23040A patent/PH14545A/en unknown
Non-Patent Citations (1)
| Title |
|---|
| NICHTS-ERMITTELT |
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| 8339 | Ceased/non-payment of the annual fee |