CA1078834A - Antifertility compounds - Google Patents
Antifertility compoundsInfo
- Publication number
- CA1078834A CA1078834A CA263,896A CA263896A CA1078834A CA 1078834 A CA1078834 A CA 1078834A CA 263896 A CA263896 A CA 263896A CA 1078834 A CA1078834 A CA 1078834A
- Authority
- CA
- Canada
- Prior art keywords
- benzoyl
- phenyl
- dihydronaphthalene
- reaction
- pyrrolidinoethoxy
- 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
- 150000001875 compounds Chemical class 0.000 title claims description 69
- 230000003509 anti-fertility effect Effects 0.000 title abstract description 10
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 31
- 150000001860 citric acid derivatives Chemical class 0.000 claims description 22
- 238000006243 chemical reaction Methods 0.000 claims description 21
- 125000003545 alkoxy group Chemical group 0.000 claims description 18
- -1 pyrrolidino, piperidino, hexamethyleneimino Chemical group 0.000 claims description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
- QJDUDPQVDAASMV-UHFFFAOYSA-M sodium;ethanethiolate Chemical compound [Na+].CC[S-] QJDUDPQVDAASMV-UHFFFAOYSA-M 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 230000000875 corresponding effect Effects 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 11
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 11
- 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 claims description 10
- 238000000034 method Methods 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 7
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 claims description 6
- KPIKJMHJFCSHEG-UHFFFAOYSA-N 1-(4-methoxybenzoyl)-3,4-dihydro-1h-naphthalen-2-one Chemical compound C1=CC(OC)=CC=C1C(=O)C1C2=CC=CC=C2CCC1=O KPIKJMHJFCSHEG-UHFFFAOYSA-N 0.000 claims description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- ANRQGKOBLBYXFM-UHFFFAOYSA-M phenylmagnesium bromide Chemical compound Br[Mg]C1=CC=CC=C1 ANRQGKOBLBYXFM-UHFFFAOYSA-M 0.000 claims description 5
- DWQHXHINSNUITH-UHFFFAOYSA-N (6-methoxy-2-phenyl-3,4-dihydronaphthalen-1-yl)-[4-(2-pyrrolidin-1-ylethoxy)phenyl]methanone Chemical compound C=1C=CC=CC=1C=1CCC2=CC(OC)=CC=C2C=1C(=O)C(C=C1)=CC=C1OCCN1CCCC1 DWQHXHINSNUITH-UHFFFAOYSA-N 0.000 claims description 4
- ULMJJYDEJBSYCY-UHFFFAOYSA-N [6-methoxy-2-(4-methoxyphenyl)-3,4-dihydronaphthalen-1-yl]-[4-(2-pyrrolidin-1-ylethoxy)phenyl]methanone Chemical compound C1=CC(OC)=CC=C1C(CCC1=CC(OC)=CC=C11)=C1C(=O)C(C=C1)=CC=C1OCCN1CCCC1 ULMJJYDEJBSYCY-UHFFFAOYSA-N 0.000 claims description 4
- UIAYNMZBJTUCDB-UHFFFAOYSA-N (2-phenylnaphthalen-1-yl)-[4-(2-pyrrolidin-1-ylethoxy)phenyl]methanone Chemical compound C=1C=CC=CC=1C=1C=CC2=CC=CC=C2C=1C(=O)C(C=C1)=CC=C1OCCN1CCCC1 UIAYNMZBJTUCDB-UHFFFAOYSA-N 0.000 claims description 3
- IHGLINDYFMDHJG-UHFFFAOYSA-N [2-(4-methoxyphenyl)-3,4-dihydronaphthalen-1-yl]-[4-(2-pyrrolidin-1-ylethoxy)phenyl]methanone Chemical compound C1=CC(OC)=CC=C1C(CCC1=CC=CC=C11)=C1C(=O)C(C=C1)=CC=C1OCCN1CCCC1 IHGLINDYFMDHJG-UHFFFAOYSA-N 0.000 claims description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
- 231100000252 nontoxic Toxicity 0.000 claims description 3
- 230000003000 nontoxic effect Effects 0.000 claims description 3
- VKPPFDPXZWFDFA-UHFFFAOYSA-N 2-chloroethanamine Chemical compound NCCCl VKPPFDPXZWFDFA-UHFFFAOYSA-N 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 239000003153 chemical reaction reagent Substances 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 6
- RMGFLMXDCGQKPS-UHFFFAOYSA-N 1-(2-chloroethyl)pyrrolidine Chemical compound ClCCN1CCCC1 RMGFLMXDCGQKPS-UHFFFAOYSA-N 0.000 claims 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 4
- YCBSFYORPSSUEP-UHFFFAOYSA-N (2-phenyl-3,4-dihydronaphthalen-1-yl)-[4-(2-pyrrolidin-1-ylethoxy)phenyl]methanone Chemical compound C=1C=C(OCCN2CCCC2)C=CC=1C(=O)C(C1=CC=CC=C1CC1)=C1C1=CC=CC=C1 YCBSFYORPSSUEP-UHFFFAOYSA-N 0.000 claims 2
- RBWRWAUAVRMBAC-UHFFFAOYSA-M magnesium;methoxybenzene;bromide Chemical compound [Mg+2].[Br-].COC1=CC=[C-]C=C1 RBWRWAUAVRMBAC-UHFFFAOYSA-M 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- ICZNPZGJAVCRIV-UHFFFAOYSA-N 6-methoxy-1-(4-phenylmethoxybenzoyl)-3,4-dihydro-1h-naphthalen-2-one Chemical compound O=C1CCC2=CC(OC)=CC=C2C1C(=O)C(C=C1)=CC=C1OCC1=CC=CC=C1 ICZNPZGJAVCRIV-UHFFFAOYSA-N 0.000 claims 1
- 230000036647 reaction Effects 0.000 claims 1
- 239000003433 contraceptive agent Substances 0.000 abstract description 9
- 239000002246 antineoplastic agent Substances 0.000 abstract description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 96
- 239000000203 mixture Substances 0.000 description 78
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 38
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 33
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 32
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 26
- 239000000047 product Substances 0.000 description 26
- 239000003921 oil Substances 0.000 description 24
- 235000019198 oils Nutrition 0.000 description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 20
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
- 239000000243 solution Substances 0.000 description 19
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 16
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 14
- 238000004458 analytical method Methods 0.000 description 14
- 239000002024 ethyl acetate extract Substances 0.000 description 13
- 241001465754 Metazoa Species 0.000 description 12
- 230000000694 effects Effects 0.000 description 12
- 238000007792 addition Methods 0.000 description 11
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 8
- 241000700159 Rattus Species 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 239000000377 silicon dioxide Substances 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 7
- 235000019341 magnesium sulphate Nutrition 0.000 description 7
- XHLHPRDBBAGVEG-UHFFFAOYSA-N 1-tetralone Chemical compound C1=CC=C2C(=O)CCCC2=C1 XHLHPRDBBAGVEG-UHFFFAOYSA-N 0.000 description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 150000002431 hydrogen Chemical group 0.000 description 6
- 239000012312 sodium hydride Substances 0.000 description 6
- 229910000104 sodium hydride Inorganic materials 0.000 description 6
- 238000004809 thin layer chromatography Methods 0.000 description 6
- 241000271566 Aves Species 0.000 description 5
- 241000282421 Canidae Species 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 230000035935 pregnancy Effects 0.000 description 5
- 239000011780 sodium chloride Substances 0.000 description 5
- 239000003981 vehicle Substances 0.000 description 5
- 235000019270 ammonium chloride Nutrition 0.000 description 4
- 210000003754 fetus Anatomy 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 238000001819 mass spectrum Methods 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- KEIFWROAQVVDBN-UHFFFAOYSA-N 1,2-dihydronaphthalene Chemical group C1=CC=C2C=CCCC2=C1 KEIFWROAQVVDBN-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 239000012458 free base Substances 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- JHCMYSXRSMHYAX-UHFFFAOYSA-N (4-methoxyphenyl)-(2-phenyl-3,4-dihydronaphthalen-1-yl)methanone Chemical compound C1=CC(OC)=CC=C1C(=O)C1=C(C=2C=CC=CC=2)CCC2=CC=CC=C12 JHCMYSXRSMHYAX-UHFFFAOYSA-N 0.000 description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-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
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 238000009395 breeding Methods 0.000 description 2
- 230000001488 breeding effect Effects 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 150000002790 naphthalenes Chemical class 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- HTNWXJOLAMOPLB-UHFFFAOYSA-N (4-hydroxyphenyl)-(2-phenylnaphthalen-1-yl)methanone Chemical compound C1=CC(O)=CC=C1C(=O)C1=C(C=2C=CC=CC=2)C=CC2=CC=CC=C12 HTNWXJOLAMOPLB-UHFFFAOYSA-N 0.000 description 1
- UNOQWPOQMYOWJF-UHFFFAOYSA-N (4-hydroxyphenyl)-[2-(4-methoxyphenyl)-3,4-dihydronaphthalen-1-yl]methanone Chemical compound C1=CC(OC)=CC=C1C(CCC1=CC=CC=C11)=C1C(=O)C1=CC=C(O)C=C1 UNOQWPOQMYOWJF-UHFFFAOYSA-N 0.000 description 1
- BMYPVFBAFZKROJ-UHFFFAOYSA-N (4-hydroxyphenyl)-[6-methoxy-2-(4-methoxyphenyl)-3,4-dihydronaphthalen-1-yl]methanone Chemical compound C1=CC(OC)=CC=C1C(CCC1=CC(OC)=CC=C11)=C1C(=O)C1=CC=C(O)C=C1 BMYPVFBAFZKROJ-UHFFFAOYSA-N 0.000 description 1
- CJEXERCBZDVOAT-UHFFFAOYSA-N (4-methoxyphenyl)-(2-phenylnaphthalen-1-yl)methanone Chemical compound C1=CC(OC)=CC=C1C(=O)C1=C(C=2C=CC=CC=2)C=CC2=CC=CC=C12 CJEXERCBZDVOAT-UHFFFAOYSA-N 0.000 description 1
- WGASWKHIQMYEHL-JWGURIENSA-N (4Z)-3,5-dibenzyl-4-benzylidene-3-hydroxyoxolan-2-one Chemical compound O=C1OC(CC=2C=CC=CC=2)\C(=C\C=2C=CC=CC=2)C1(O)CC1=CC=CC=C1 WGASWKHIQMYEHL-JWGURIENSA-N 0.000 description 1
- SMQYCDGSSRCWKM-UHFFFAOYSA-N (6-ethoxy-2-phenyl-3,4-dihydronaphthalen-1-yl)-[4-(2-pyrrolidin-1-ylethoxy)phenyl]methanone Chemical compound C=1C=CC=CC=1C=1CCC2=CC(OCC)=CC=C2C=1C(=O)C(C=C1)=CC=C1OCCN1CCCC1 SMQYCDGSSRCWKM-UHFFFAOYSA-N 0.000 description 1
- VYVFEMFBBUVMRE-UHFFFAOYSA-N (6-hydroxy-2-phenylnaphthalen-1-yl)-[4-(2-pyrrolidin-1-ylethoxy)phenyl]methanone Chemical compound C=1C=CC=CC=1C=1C=CC2=CC(O)=CC=C2C=1C(=O)C(C=C1)=CC=C1OCCN1CCCC1 VYVFEMFBBUVMRE-UHFFFAOYSA-N 0.000 description 1
- JMVRCVARJWFEAH-UHFFFAOYSA-N (6-methoxy-2-phenylnaphthalen-1-yl)-[4-(2-morpholin-4-ylethoxy)phenyl]methanone Chemical compound C=1C=CC=CC=1C=1C=CC2=CC(OC)=CC=C2C=1C(=O)C(C=C1)=CC=C1OCCN1CCOCC1 JMVRCVARJWFEAH-UHFFFAOYSA-N 0.000 description 1
- JESBFJDGEGXURN-UHFFFAOYSA-N (6-methoxy-2-phenylnaphthalen-1-yl)-[4-(2-pyrrolidin-1-ylethoxy)phenyl]methanone Chemical compound C=1C=CC=CC=1C=1C=CC2=CC(OC)=CC=C2C=1C(=O)C(C=C1)=CC=C1OCCN1CCCC1 JESBFJDGEGXURN-UHFFFAOYSA-N 0.000 description 1
- CWLSQIXOLLQBDC-HWKANZROSA-N (e)-3-[4-hydroxy-3-(2-hydroxy-5-prop-2-enylphenyl)phenyl]prop-2-enal Chemical compound OC1=CC=C(CC=C)C=C1C1=CC(\C=C\C=O)=CC=C1O CWLSQIXOLLQBDC-HWKANZROSA-N 0.000 description 1
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 1
- TVZQDMRKJSXJPZ-UHFFFAOYSA-N 1,2-dihydronaphthalen-1-ol Chemical compound C1=CC=C2C(O)CC=CC2=C1 TVZQDMRKJSXJPZ-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 229940005561 1,4-benzoquinone Drugs 0.000 description 1
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical class C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 1
- PQLILXUGXMAYAV-UHFFFAOYSA-N 1-ethoxy-1,2-dihydronaphthalene Chemical compound C1=CC=C2C(OCC)CC=CC2=C1 PQLILXUGXMAYAV-UHFFFAOYSA-N 0.000 description 1
- NRJUDVPOGVERHI-UHFFFAOYSA-N 2-methylidene-1,3,5-triphenylpentane-1,5-dione Chemical compound C=1C=CC=CC=1C(=O)C(=C)C(C=1C=CC=CC=1)CC(=O)C1=CC=CC=C1 NRJUDVPOGVERHI-UHFFFAOYSA-N 0.000 description 1
- XMIYCZUIHNVBKA-UHFFFAOYSA-N 2-pentoxynaphthalene Chemical compound C1=CC=CC2=CC(OCCCCC)=CC=C21 XMIYCZUIHNVBKA-UHFFFAOYSA-N 0.000 description 1
- 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 1
- GJGFBYJWKQSWNO-UHFFFAOYSA-N 4-(3,4-dihydronaphthalen-2-yl)phenol Chemical class C1=CC(O)=CC=C1C1=CC2=CC=CC=C2CC1 GJGFBYJWKQSWNO-UHFFFAOYSA-N 0.000 description 1
- QJPJQTDYNZXKQF-UHFFFAOYSA-N 4-bromoanisole Chemical compound COC1=CC=C(Br)C=C1 QJPJQTDYNZXKQF-UHFFFAOYSA-N 0.000 description 1
- RMRKDYNVZWKAFP-UHFFFAOYSA-N 6-methoxy-3,4-dihydro-1h-naphthalen-2-one Chemical compound C1C(=O)CCC2=CC(OC)=CC=C21 RMRKDYNVZWKAFP-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
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241000272201 Columbiformes Species 0.000 description 1
- 238000003747 Grignard reaction Methods 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 101100400378 Mus musculus Marveld2 gene Proteins 0.000 description 1
- RSPISYXLHRIGJD-UHFFFAOYSA-N OOOO Chemical compound OOOO RSPISYXLHRIGJD-UHFFFAOYSA-N 0.000 description 1
- 208000032749 Pregnancy Diseases 0.000 description 1
- 241000283984 Rodentia Species 0.000 description 1
- 241000287182 Sturnidae Species 0.000 description 1
- 241000962283 Turdus iliacus Species 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- ZXVLAULOUIYCEO-UHFFFAOYSA-N [2-(4-ethoxyphenyl)-3,4-dihydronaphthalen-1-yl]-[4-(2-morpholin-4-ylethoxy)phenyl]methanone Chemical compound C1=CC(OCC)=CC=C1C(CCC1=CC=CC=C11)=C1C(=O)C(C=C1)=CC=C1OCCN1CCOCC1 ZXVLAULOUIYCEO-UHFFFAOYSA-N 0.000 description 1
- NVXCYRALHVOUSP-UHFFFAOYSA-N [2-(4-ethoxyphenyl)-3,4-dihydronaphthalen-1-yl]-[4-(2-pyrrolidin-1-ylethoxy)phenyl]methanone Chemical compound C1=CC(OCC)=CC=C1C(CCC1=CC=CC=C11)=C1C(=O)C(C=C1)=CC=C1OCCN1CCCC1 NVXCYRALHVOUSP-UHFFFAOYSA-N 0.000 description 1
- BHYMNKAYMWYDON-UHFFFAOYSA-N [2-(4-ethoxyphenyl)naphthalen-1-yl]-[4-(2-morpholin-4-ylethoxy)phenyl]methanone Chemical compound C1=CC(OCC)=CC=C1C1=CC=C(C=CC=C2)C2=C1C(=O)C(C=C1)=CC=C1OCCN1CCOCC1 BHYMNKAYMWYDON-UHFFFAOYSA-N 0.000 description 1
- RCKWKNJERAIQMI-UHFFFAOYSA-N [2-(4-hydroxyphenyl)naphthalen-1-yl]-[4-(2-pyrrolidin-1-ylethoxy)phenyl]methanone Chemical compound C1=CC(O)=CC=C1C1=CC=C(C=CC=C2)C2=C1C(=O)C(C=C1)=CC=C1OCCN1CCCC1 RCKWKNJERAIQMI-UHFFFAOYSA-N 0.000 description 1
- VVTOZHSGDQNHDR-UHFFFAOYSA-N [2-(4-methoxyphenyl)-3,4-dihydronaphthalen-1-yl]-[4-(2-piperidin-1-ylethoxy)phenyl]methanone Chemical compound C1=CC(OC)=CC=C1C(CCC1=CC=CC=C11)=C1C(=O)C(C=C1)=CC=C1OCCN1CCCCC1 VVTOZHSGDQNHDR-UHFFFAOYSA-N 0.000 description 1
- KZTLMNCDYAOUAN-UHFFFAOYSA-N [2-(4-pentoxyphenyl)-3,4-dihydronaphthalen-1-yl]-[4-(2-piperidin-1-ylethoxy)phenyl]methanone Chemical compound C1=CC(OCCCCC)=CC=C1C(CCC1=CC=CC=C11)=C1C(=O)C(C=C1)=CC=C1OCCN1CCCCC1 KZTLMNCDYAOUAN-UHFFFAOYSA-N 0.000 description 1
- YFUZPXHUTKLSCI-UHFFFAOYSA-N [2-(4-pentoxyphenyl)naphthalen-1-yl]-[4-(2-piperidin-1-ylethoxy)phenyl]methanone Chemical compound C1=CC(OCCCCC)=CC=C1C1=CC=C(C=CC=C2)C2=C1C(=O)C(C=C1)=CC=C1OCCN1CCCCC1 YFUZPXHUTKLSCI-UHFFFAOYSA-N 0.000 description 1
- BPVBOMVKZPJDLH-UHFFFAOYSA-N [2-(4-propoxyphenyl)-3,4-dihydronaphthalen-1-yl]-[4-(2-pyrrolidin-1-ylethoxy)phenyl]methanone Chemical compound C1=CC(OCCC)=CC=C1C(CCC1=CC=CC=C11)=C1C(=O)C(C=C1)=CC=C1OCCN1CCCC1 BPVBOMVKZPJDLH-UHFFFAOYSA-N 0.000 description 1
- IMRGNRKLHIUBRO-UHFFFAOYSA-N [2-[4-[(2-methylpropan-2-yl)oxy]phenyl]naphthalen-1-yl]-[4-(2-pyrrolidin-1-ylethoxy)phenyl]methanone Chemical compound C1=CC(OC(C)(C)C)=CC=C1C1=CC=C(C=CC=C2)C2=C1C(=O)C(C=C1)=CC=C1OCCN1CCCC1 IMRGNRKLHIUBRO-UHFFFAOYSA-N 0.000 description 1
- DEBGRJKCDGUPRG-UHFFFAOYSA-N [4-(2-morpholin-4-ylethoxy)phenyl]-(2-phenyl-6-propan-2-yloxy-3,4-dihydronaphthalen-1-yl)methanone Chemical compound C=1C=CC=CC=1C=1CCC2=CC(OC(C)C)=CC=C2C=1C(=O)C(C=C1)=CC=C1OCCN1CCOCC1 DEBGRJKCDGUPRG-UHFFFAOYSA-N 0.000 description 1
- LXFKNAJNCVZHCZ-UHFFFAOYSA-N [4-(2-morpholin-4-ylethoxy)phenyl]-[2-(4-pentoxyphenyl)naphthalen-1-yl]methanone Chemical compound C1=CC(OCCCCC)=CC=C1C1=CC=C(C=CC=C2)C2=C1C(=O)C(C=C1)=CC=C1OCCN1CCOCC1 LXFKNAJNCVZHCZ-UHFFFAOYSA-N 0.000 description 1
- QHNQCDWEIPDVRR-UHFFFAOYSA-N [4-[2-(azepan-1-yl)ethoxy]phenyl]-(6-methoxy-2-phenylnaphthalen-1-yl)methanone Chemical compound C=1C=CC=CC=1C=1C=CC2=CC(OC)=CC=C2C=1C(=O)C(C=C1)=CC=C1OCCN1CCCCCC1 QHNQCDWEIPDVRR-UHFFFAOYSA-N 0.000 description 1
- YXBZGWVABGTDKV-UHFFFAOYSA-N [4-[2-(azepan-1-yl)ethoxy]phenyl]-[2-(4-hydroxyphenyl)naphthalen-1-yl]methanone Chemical compound C1=CC(O)=CC=C1C1=CC=C(C=CC=C2)C2=C1C(=O)C(C=C1)=CC=C1OCCN1CCCCCC1 YXBZGWVABGTDKV-UHFFFAOYSA-N 0.000 description 1
- ODKTXBFMSOGDLS-UHFFFAOYSA-N [4-[2-(azepan-1-yl)ethoxy]phenyl]-[2-[4-[(2-methylpropan-2-yl)oxy]phenyl]naphthalen-1-yl]methanone Chemical compound C1=CC(OC(C)(C)C)=CC=C1C1=CC=C(C=CC=C2)C2=C1C(=O)C(C=C1)=CC=C1OCCN1CCCCCC1 ODKTXBFMSOGDLS-UHFFFAOYSA-N 0.000 description 1
- ZTMJCYWALAPHBK-UHFFFAOYSA-N [4-[2-(diethylamino)ethoxy]phenyl]-(6-hydroxy-2-phenyl-3,4-dihydronaphthalen-1-yl)methanone Chemical compound C1=CC(OCCN(CC)CC)=CC=C1C(=O)C1=C(C=2C=CC=CC=2)CCC2=CC(O)=CC=C12 ZTMJCYWALAPHBK-UHFFFAOYSA-N 0.000 description 1
- CXDWYKRNTKAEHZ-UHFFFAOYSA-N [4-[2-(diethylamino)ethoxy]phenyl]-[2-(4-methoxyphenyl)naphthalen-1-yl]methanone Chemical compound C1=CC(OCCN(CC)CC)=CC=C1C(=O)C1=C(C=2C=CC(OC)=CC=2)C=CC2=CC=CC=C12 CXDWYKRNTKAEHZ-UHFFFAOYSA-N 0.000 description 1
- AGXVURWLPUOUOV-UHFFFAOYSA-N [4-[2-(diethylamino)ethoxy]phenyl]-[6-methoxy-2-(4-methoxyphenyl)naphthalen-1-yl]methanone Chemical compound C1=CC(OCCN(CC)CC)=CC=C1C(=O)C1=C(C=2C=CC(OC)=CC=2)C=CC2=CC(OC)=CC=C12 AGXVURWLPUOUOV-UHFFFAOYSA-N 0.000 description 1
- YKKJXOMUUKFBJJ-UHFFFAOYSA-N [4-[2-(dimethylamino)ethoxy]phenyl]-(6-hydroxy-2-phenyl-3,4-dihydronaphthalen-1-yl)methanone Chemical compound C1=CC(OCCN(C)C)=CC=C1C(=O)C1=C(C=2C=CC=CC=2)CCC2=CC(O)=CC=C12 YKKJXOMUUKFBJJ-UHFFFAOYSA-N 0.000 description 1
- FHEHRNDMWRXNEH-UHFFFAOYSA-N [4-[2-(dimethylamino)ethoxy]phenyl]-(6-hydroxy-2-phenylnaphthalen-1-yl)methanone Chemical compound C1=CC(OCCN(C)C)=CC=C1C(=O)C1=C(C=2C=CC=CC=2)C=CC2=CC(O)=CC=C12 FHEHRNDMWRXNEH-UHFFFAOYSA-N 0.000 description 1
- CCGRDPQJBLPZMN-UHFFFAOYSA-N [4-[2-(dimethylamino)ethoxy]phenyl]-[2-(4-methoxyphenyl)naphthalen-1-yl]methanone Chemical compound C1=CC(OC)=CC=C1C1=CC=C(C=CC=C2)C2=C1C(=O)C1=CC=C(OCCN(C)C)C=C1 CCGRDPQJBLPZMN-UHFFFAOYSA-N 0.000 description 1
- PRNSRAJWSNRESU-UHFFFAOYSA-N [4-[2-(dimethylamino)ethoxy]phenyl]-[2-(4-propoxyphenyl)-3,4-dihydronaphthalen-1-yl]methanone Chemical compound C1=CC(OCCC)=CC=C1C(CCC1=CC=CC=C11)=C1C(=O)C1=CC=C(OCCN(C)C)C=C1 PRNSRAJWSNRESU-UHFFFAOYSA-N 0.000 description 1
- AQOHFYCOIZLNJA-UHFFFAOYSA-N [4-[2-(dimethylamino)ethoxy]phenyl]-[2-(4-propoxyphenyl)naphthalen-1-yl]methanone Chemical compound C1=CC(OCCC)=CC=C1C1=CC=C(C=CC=C2)C2=C1C(=O)C1=CC=C(OCCN(C)C)C=C1 AQOHFYCOIZLNJA-UHFFFAOYSA-N 0.000 description 1
- CJKPSPGYSLRHEK-UHFFFAOYSA-N [4-[2-(dimethylamino)ethoxy]phenyl]-[2-[4-[(2-methylpropan-2-yl)oxy]phenyl]-6-propoxynaphthalen-1-yl]methanone Chemical compound C=1C=C(OC(C)(C)C)C=CC=1C=1C=CC2=CC(OCCC)=CC=C2C=1C(=O)C1=CC=C(OCCN(C)C)C=C1 CJKPSPGYSLRHEK-UHFFFAOYSA-N 0.000 description 1
- MZWRKEDYYZMUFF-UHFFFAOYSA-N [4-[2-(dimethylamino)ethoxy]phenyl]-[6-hydroxy-2-(4-hydroxyphenyl)-3,4-dihydronaphthalen-1-yl]methanone Chemical compound C1=CC(OCCN(C)C)=CC=C1C(=O)C1=C(C=2C=CC(O)=CC=2)CCC2=CC(O)=CC=C12 MZWRKEDYYZMUFF-UHFFFAOYSA-N 0.000 description 1
- JREMOFJBYZEUFN-UHFFFAOYSA-N [6-ethoxy-2-(4-ethoxyphenyl)-3,4-dihydronaphthalen-1-yl]-[4-(2-morpholin-4-ylethoxy)phenyl]methanone Chemical compound C1=CC(OCC)=CC=C1C(CCC1=CC(OCC)=CC=C11)=C1C(=O)C(C=C1)=CC=C1OCCN1CCOCC1 JREMOFJBYZEUFN-UHFFFAOYSA-N 0.000 description 1
- DWKRSSGLEQWZQK-UHFFFAOYSA-N [6-ethoxy-2-(4-ethoxyphenyl)naphthalen-1-yl]-[4-(2-morpholin-4-ylethoxy)phenyl]methanone Chemical compound C1=CC(OCC)=CC=C1C1=CC=C(C=C(OCC)C=C2)C2=C1C(=O)C(C=C1)=CC=C1OCCN1CCOCC1 DWKRSSGLEQWZQK-UHFFFAOYSA-N 0.000 description 1
- AYNIPIYJGWHUBW-UHFFFAOYSA-N [6-ethoxy-2-(4-propan-2-yloxyphenyl)-3,4-dihydronaphthalen-1-yl]-[4-(2-pyrrolidin-1-ylethoxy)phenyl]methanone Chemical compound C=1C=C(OC(C)C)C=CC=1C=1CCC2=CC(OCC)=CC=C2C=1C(=O)C(C=C1)=CC=C1OCCN1CCCC1 AYNIPIYJGWHUBW-UHFFFAOYSA-N 0.000 description 1
- KRULEDWAJRZCIA-UHFFFAOYSA-N [6-methoxy-2-(4-methoxyphenyl)-3,4-dihydronaphthalen-1-yl]-(4-phenylmethoxyphenyl)methanone Chemical compound C1=CC(OC)=CC=C1C(CCC1=CC(OC)=CC=C11)=C1C(=O)C(C=C1)=CC=C1OCC1=CC=CC=C1 KRULEDWAJRZCIA-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000005667 attractant Substances 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- JYYOBHFYCIDXHH-UHFFFAOYSA-N carbonic acid;hydrate Chemical compound O.OC(O)=O JYYOBHFYCIDXHH-UHFFFAOYSA-N 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 229940124558 contraceptive agent Drugs 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000002285 corn oil Substances 0.000 description 1
- 235000005687 corn oil Nutrition 0.000 description 1
- 239000013058 crude material Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 230000017858 demethylation Effects 0.000 description 1
- 238000010520 demethylation reaction Methods 0.000 description 1
- 125000001891 dimethoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 230000003292 diminished effect Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 230000035558 fertility Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- 238000002513 implantation Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229910003480 inorganic solid Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 239000008177 pharmaceutical agent Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- CBQVOBIZPAFTDN-UHFFFAOYSA-N phenyl 4-(2-pyrrolidin-1-ylethoxy)benzoate Chemical compound C=1C=C(OCCN2CCCC2)C=CC=1C(=O)OC1=CC=CC=C1 CBQVOBIZPAFTDN-UHFFFAOYSA-N 0.000 description 1
- GJLNWLVPAHNBQN-UHFFFAOYSA-N phenyl 4-hydroxybenzoate Chemical compound C1=CC(O)=CC=C1C(=O)OC1=CC=CC=C1 GJLNWLVPAHNBQN-UHFFFAOYSA-N 0.000 description 1
- BNZYBNYNPXKWCM-UHFFFAOYSA-N phenyl 4-methoxybenzoate Chemical compound C1=CC(OC)=CC=C1C(=O)OC1=CC=CC=C1 BNZYBNYNPXKWCM-UHFFFAOYSA-N 0.000 description 1
- FCJSHPDYVMKCHI-UHFFFAOYSA-N phenyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OC1=CC=CC=C1 FCJSHPDYVMKCHI-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- RBWSWDPRDBEWCR-RKJRWTFHSA-N sodium;(2r)-2-[(2r)-3,4-dihydroxy-5-oxo-2h-furan-2-yl]-2-hydroxyethanolate Chemical compound [Na+].[O-]C[C@@H](O)[C@H]1OC(=O)C(O)=C1O RBWSWDPRDBEWCR-RKJRWTFHSA-N 0.000 description 1
- 230000003637 steroidlike Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 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
- 210000001215 vagina Anatomy 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- 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
- C07C45/455—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation with carboxylic acids or their derivatives
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- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/82—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups
- C07C49/83—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups polycyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/235—Saturated compounds containing more than one carboxyl group
- C07C59/245—Saturated compounds containing more than one carboxyl group containing hydroxy or O-metal groups
- C07C59/265—Citric acid
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Tropical Medicine & Parasitology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Indole Compounds (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US62599175A | 1975-10-28 | 1975-10-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1078834A true CA1078834A (en) | 1980-06-03 |
Family
ID=24508491
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA263,896A Expired CA1078834A (en) | 1975-10-28 | 1976-10-21 | Antifertility compounds |
Country Status (30)
| Country | Link |
|---|---|
| JP (1) | JPS6045191B2 (cs) |
| AR (1) | AR214622A1 (cs) |
| AT (1) | AT346321B (cs) |
| AU (1) | AU509372B2 (cs) |
| BE (1) | BE847716A (cs) |
| BG (1) | BG27555A3 (cs) |
| CA (1) | CA1078834A (cs) |
| CH (2) | CH624398A5 (cs) |
| CS (1) | CS235057B2 (cs) |
| DD (1) | DD127460A5 (cs) |
| DE (1) | DE2646213C2 (cs) |
| DK (1) | DK484776A (cs) |
| ES (1) | ES452735A1 (cs) |
| FR (1) | FR2329264A1 (cs) |
| GB (1) | GB1561687A (cs) |
| GR (1) | GR61816B (cs) |
| HU (1) | HU175227B (cs) |
| IE (1) | IE43641B1 (cs) |
| IL (1) | IL50772A (cs) |
| MX (1) | MX4291E (cs) |
| NL (1) | NL187164C (cs) |
| NZ (1) | NZ182421A (cs) |
| PH (1) | PH14538A (cs) |
| PL (2) | PL104551B1 (cs) |
| PT (1) | PT65752B (cs) |
| RO (1) | RO70755A (cs) |
| SE (1) | SE428689B (cs) |
| SU (2) | SU791220A3 (cs) |
| YU (1) | YU262276A (cs) |
| ZA (1) | ZA766439B (cs) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4179558A (en) * | 1978-01-30 | 1979-12-18 | E. R. Squibb & Sons, Inc. | Naphthalenone derivatives and analogs |
| DE3121175A1 (de) * | 1981-05-27 | 1982-12-16 | Klinge Pharma GmbH, 8000 München | Erythro-1,2,3-triphenyl-1-pentanon-derivate sowie verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
| US4410553A (en) | 1981-08-28 | 1983-10-18 | Mcginty James | Method and apparatus for cooking particulate foodstuffs |
| JPH0717589B2 (ja) * | 1990-01-22 | 1995-03-01 | ファイザー製薬株式会社 | 新規１，３―ジカルボニル化合物およびその組成物 |
| US6391892B1 (en) * | 1995-03-10 | 2002-05-21 | Eli Lilly And Company | Naphthyl pharmaceutical compounds |
-
1976
- 1976-10-13 DE DE2646213A patent/DE2646213C2/de not_active Expired
- 1976-10-20 MX MX764988U patent/MX4291E/es unknown
- 1976-10-21 NZ NZ182421A patent/NZ182421A/xx unknown
- 1976-10-21 CA CA263,896A patent/CA1078834A/en not_active Expired
- 1976-10-22 PH PH19030A patent/PH14538A/en unknown
- 1976-10-22 GB GB43884/76A patent/GB1561687A/en not_active Expired
- 1976-10-25 PT PT65752A patent/PT65752B/pt unknown
- 1976-10-25 GR GR52004A patent/GR61816B/el unknown
- 1976-10-26 RO RO7688227A patent/RO70755A/ro unknown
- 1976-10-26 SU SU762414461A patent/SU791220A3/ru active
- 1976-10-26 ES ES452735A patent/ES452735A1/es not_active Expired
- 1976-10-26 PL PL1976193264A patent/PL104551B1/pl unknown
- 1976-10-26 PL PL1976211453A patent/PL111987B1/pl unknown
- 1976-10-26 AU AU19004/76A patent/AU509372B2/en not_active Expired
- 1976-10-26 JP JP51129305A patent/JPS6045191B2/ja not_active Expired
- 1976-10-27 IL IL50772A patent/IL50772A/xx unknown
- 1976-10-27 DK DK484776A patent/DK484776A/da not_active Application Discontinuation
- 1976-10-27 IE IE2371/76A patent/IE43641B1/en unknown
- 1976-10-27 YU YU02622/76A patent/YU262276A/xx unknown
- 1976-10-27 CH CH1355476A patent/CH624398A5/de not_active IP Right Cessation
- 1976-10-27 HU HU76EI716A patent/HU175227B/hu unknown
- 1976-10-27 ZA ZA00766439A patent/ZA766439B/xx unknown
- 1976-10-27 SE SE7611953A patent/SE428689B/xx not_active IP Right Cessation
- 1976-10-28 BE BE1007722A patent/BE847716A/xx not_active IP Right Cessation
- 1976-10-28 AR AR265274A patent/AR214622A1/es active
- 1976-10-28 FR FR7632511A patent/FR2329264A1/fr active Granted
- 1976-10-28 CS CS766971A patent/CS235057B2/cs unknown
- 1976-10-28 AT AT800576A patent/AT346321B/de not_active IP Right Cessation
- 1976-10-28 BG BG034552A patent/BG27555A3/xx unknown
- 1976-10-28 NL NLAANVRAGE7611974,A patent/NL187164C/xx not_active IP Right Cessation
- 1976-10-28 DD DD195507A patent/DD127460A5/xx unknown
-
1978
- 1978-07-25 SU SU782641053A patent/SU818476A3/ru active
-
1980
- 1980-08-28 CH CH648780A patent/CH624376A5/de not_active IP Right Cessation
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |