CH624375A5 - - Google Patents

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Info

Publication number: CH624375A5
Authority: CH; Switzerland
Prior art keywords: compounds; formula; phenyl; mixture; acid
Prior art date: 1975-10-28

Application number

CH1355276A

Other languages

German (de)

English (en)

Inventor

Tulio Suarez

Charles David Jones

Original Assignee

Lilly Co Eli

Priority date (The priority date 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 date listed.)

1975-10-28

Filing date

1976-10-27

Publication date

1981-07-31

1976-10-27 Application filed by Lilly Co Eli filed Critical Lilly Co Eli

1981-07-31 Publication of CH624375A5 publication Critical patent/CH624375A5/de

Links

-1 4-hydroxybenzoyl Chemical group 0.000 claims description 16
238000000034 method Methods 0.000 claims description 13
238000002360 preparation method Methods 0.000 claims description 11
ANRQGKOBLBYXFM-UHFFFAOYSA-M phenylmagnesium bromide Chemical compound Br[Mg]C1=CC=CC=C1 ANRQGKOBLBYXFM-UHFFFAOYSA-M 0.000 claims description 10
150000001875 compounds Chemical class 0.000 description 43
239000000203 mixture Substances 0.000 description 27
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
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
241001465754 Metazoa Species 0.000 description 14
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
239000000243 solution Substances 0.000 description 12
239000002253 acid Substances 0.000 description 10
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
150000003839 salts Chemical class 0.000 description 8
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
125000003545 alkoxy group Chemical group 0.000 description 7
239000000155 melt Substances 0.000 description 7
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
241000700159 Rattus Species 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
230000003509 anti-fertility effect Effects 0.000 description 6
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
230000035558 fertility Effects 0.000 description 6
125000001424 substituent group Chemical group 0.000 description 6
241000282421 Canidae Species 0.000 description 5
238000004458 analytical method Methods 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
229910052739 hydrogen Inorganic materials 0.000 description 5
239000001257 hydrogen Substances 0.000 description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
230000002401 inhibitory effect Effects 0.000 description 5
231100000252 nontoxic Toxicity 0.000 description 5
230000003000 nontoxic effect Effects 0.000 description 5
230000035935 pregnancy Effects 0.000 description 5
239000002002 slurry Substances 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
125000001999 4-Methoxybenzoyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C(*)=O 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
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
239000004480 active ingredient Substances 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
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 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
239000003433 contraceptive agent Substances 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
239000000047 product Substances 0.000 description 3
238000010992 reflux Methods 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
239000000725 suspension Substances 0.000 description 3
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
241000124008 Mammalia Species 0.000 description 2
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
230000037396 body weight Effects 0.000 description 2
ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 2
238000003776 cleavage reaction Methods 0.000 description 2
238000013329 compounding Methods 0.000 description 2
238000001816 cooling Methods 0.000 description 2
238000001914 filtration Methods 0.000 description 2
238000009472 formulation Methods 0.000 description 2
150000002431 hydrogen Chemical class 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
238000001819 mass spectrum Methods 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
239000002244 precipitate Substances 0.000 description 2
AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
230000007017 scission Effects 0.000 description 2
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 2
QJDUDPQVDAASMV-UHFFFAOYSA-M sodium;ethanethiolate Chemical compound [Na+].CC[S-] QJDUDPQVDAASMV-UHFFFAOYSA-M 0.000 description 2
239000007787 solid Substances 0.000 description 2
150000003431 steroids Chemical class 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
238000005303 weighing Methods 0.000 description 2
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
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
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
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 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
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 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
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
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
FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical class C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 1
XHLHPRDBBAGVEG-UHFFFAOYSA-N 1-tetralone Chemical compound C1=CC=C2C(=O)CCCC2=C1 XHLHPRDBBAGVEG-UHFFFAOYSA-N 0.000 description 1
PANZFQYXPMCHFD-UHFFFAOYSA-N 2,3-diphenyl-1h-indene Chemical compound C12=CC=CC=C2CC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 PANZFQYXPMCHFD-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
BJJQJLOZWBZEGA-UHFFFAOYSA-N 3-Methoxybenzenepropanoic acid Chemical compound COC1=CC=CC(CCC(O)=O)=C1 BJJQJLOZWBZEGA-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-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
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
241000282472 Canis lupus familiaris Species 0.000 description 1
241000272161 Charadriiformes Species 0.000 description 1
241000272201 Columbiformes Species 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
241000283984 Rodentia Species 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 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
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-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
239000003513 alkali Substances 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
239000005667 attractant Substances 0.000 description 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
239000002775 capsule Substances 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000012876 carrier material Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
238000013375 chromatographic separation Methods 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
229940124558 contraceptive agent Drugs 0.000 description 1
239000002285 corn oil Substances 0.000 description 1
235000005687 corn oil Nutrition 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
239000002552 dosage form Substances 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
230000000694 effects Effects 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
239000001530 fumaric acid Substances 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
229910003480 inorganic solid Inorganic materials 0.000 description 1
239000010410 layer Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
229940126601 medicinal product Drugs 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
150000007524 organic acids Chemical class 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
239000000843 powder Substances 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
238000006798 ring closing metathesis reaction Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 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)

CH1355276A 1975-10-28 1976-10-27 CH624375A5 (fr)

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 (1)

Publication Number	Publication Date
CH624375A5 true CH624375A5 (fr)	1981-07-31

Family

ID=24508497

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1355276A CH624375A5 (fr)	1975-10-28	1976-10-27

Country Status (31)

Country	Link
US (2)	US4017546A (fr)
JP (1)	JPS5253844A (fr)
AR (1)	AR221031A1 (fr)
AT (1)	AT347443B (fr)
AU (1)	AU503883B2 (fr)
BE (1)	BE847717A (fr)
BG (1)	BG27556A3 (fr)
CA (1)	CA1064926A (fr)
CH (1)	CH624375A5 (fr)
CS (1)	CS234003B2 (fr)
DD (1)	DD127462A5 (fr)
DE (1)	DE2647906C2 (fr)
DK (1)	DK484676A (fr)
ES (1)	ES452736A1 (fr)
FR (1)	FR2329265A1 (fr)
GB (1)	GB1562806A (fr)
GR (1)	GR61239B (fr)
HU (1)	HU176092B (fr)
IE (1)	IE43642B1 (fr)
IL (1)	IL50414A (fr)
MX (1)	MX4320E (fr)
NL (1)	NL7611973A (fr)
NZ (1)	NZ182426A (fr)
PH (2)	PH13486A (fr)
PL (1)	PL106987B1 (fr)
PT (1)	PT65754B (fr)
RO (1)	RO70754A (fr)
SE (1)	SE431086B (fr)
SU (1)	SU654164A3 (fr)
YU (1)	YU262176A (fr)
ZA (1)	ZA766441B (fr)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4323707A (en) *	1975-10-28	1982-04-06	Eli Lilly And Company	Antifertility compounds
US4230862A (en) *	1975-10-28	1980-10-28	Eli Lilly And Company	Antifertility compounds
US4017546A (en) *	1975-10-28	1977-04-12	Eli Lilly And Company	Novel antifertility agents
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)

* Cited by examiner, † Cited by third party
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 MX MX764987U patent/MX4320E/es unknown
- 1976-10-20 JP JP51126786A patent/JPS5253844A/ja active Granted
- 1976-10-21 NZ NZ182426A patent/NZ182426A/xx unknown
- 1976-10-21 CA CA263,843A patent/CA1064926A/fr 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 GR GR52002A patent/GR61239B/el unknown
- 1976-10-25 PT PT65754A patent/PT65754B/pt unknown
- 1976-10-25 GB GB44176/76A patent/GB1562806A/en not_active Expired
- 1976-10-26 SU SU762414100A patent/SU654164A3/ru active
- 1976-10-26 RO RO7688225A patent/RO70754A/fr unknown
- 1976-10-26 ES ES452736A patent/ES452736A1/es not_active Expired
- 1976-10-27 CH CH1355276A patent/CH624375A5/de not_active IP Right Cessation
- 1976-10-27 IE IE2373/76A patent/IE43642B1/en unknown
- 1976-10-27 YU YU02621/76A patent/YU262176A/xx unknown
- 1976-10-27 SE SE7611952A patent/SE431086B/xx not_active IP Right Cessation
- 1976-10-27 DK DK484676A patent/DK484676A/da not_active Application Discontinuation
- 1976-10-27 ZA ZA00766441A patent/ZA766441B/xx unknown
- 1976-10-28 CS CS766972A patent/CS234003B2/cs unknown
- 1976-10-28 BG BG034553A patent/BG27556A3/xx unknown
- 1976-10-28 NL NL7611973A patent/NL7611973A/xx not_active Application Discontinuation
- 1976-10-28 FR FR7632512A patent/FR2329265A1/fr active Granted
- 1976-10-28 BE BE1007723A patent/BE847717A/fr not_active IP Right Cessation
- 1976-10-28 AT AT800676A patent/AT347443B/de not_active IP Right Cessation
- 1976-10-28 AR AR265275A patent/AR221031A1/es active
- 1976-10-28 DD DD195509A patent/DD127462A5/xx unknown
- 1976-10-28 PL PL1976193327A patent/PL106987B1/pl unknown
- 1976-11-24 US US05/744,488 patent/US4075223A/en not_active Expired - Lifetime
1979
- 1979-09-17 PH PH23040A patent/PH14545A/en unknown

Also Published As

Publication number	Publication date
ATA800676A (de)	1978-05-15
SE431086B (sv)	1984-01-16
ES452736A1 (es)	1978-01-16
PH13486A (en)	1980-05-21
HU176092B (en)	1980-12-28
YU262176A (en)	1982-05-31
ZA766441B (en)	1978-06-28
DE2647906C2 (de)	1985-01-31
DD127462A5 (fr)	1977-09-28
GR61239B (en)	1978-10-12
PL106987B1 (pl)	1980-01-31
US4075223A (en)	1978-02-21
RO70754A (fr)	1982-10-26
IE43642L (en)	1977-04-28
MX4320E (es)	1982-03-24
FR2329265B1 (fr)	1980-05-16
PH14545A (en)	1981-09-24
BG27556A3 (en)	1979-11-12
PT65754B (en)	1978-04-27
IL50414A (en)	1980-09-16
AU1740776A (en)	1978-03-09
SU654164A3 (ru)	1979-03-25
AR221031A1 (es)	1980-12-30
PT65754A (en)	1976-11-01
JPS5253844A (en)	1977-04-30
IL50414A0 (en)	1976-11-30
SE7611952L (sv)	1977-04-29
GB1562806A (en)	1980-03-19
CA1064926A (fr)	1979-10-23
IE43642B1 (en)	1981-04-22
DE2647906A1 (de)	1977-05-05
CS234003B2 (en)	1985-03-14
AT347443B (de)	1978-12-27
NL7611973A (nl)	1977-05-02
FR2329265A1 (fr)	1977-05-27
BE847717A (fr)	1977-04-28
DK484676A (da)	1977-04-29
NZ182426A (en)	1978-11-13
AU503883B2 (en)	1979-09-27
US4017546A (en)	1977-04-12
JPS6114141B2 (fr)	1986-04-17

Legal Events

Date	Code	Title	Description
1989-06-30	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
DE2647907C2 (de)	1985-01-24	2-Phenyl-3-aroylbenzothiophene und Verfahren zu ihrer Herstellung
DE2647864C2 (de)	1985-04-25	2-Aroyl-3-phenylbenzothiophenverbindungen und Verfahren zu ihrer Herstellung
EP0013376B1 (fr)	1982-05-19	Dérivé d'isoxazole, procédé pour sa préparation et composition le contenant
EP0004279B1 (fr)	1982-12-29	Procédé pour la préparation d'acides 4-pyridone-3-carboxyliques, dérivés d'acides 1-cyclopropyl-4-pyridone-3-carboxyliques et médicament les contenant
EP0315071B1 (fr)	1994-07-20	Dérivés de benzocycloheptène, leur préparation et utilisation comme agents pharmaceutiques
DE3033157A1 (de)	1982-04-01	7-amino-1-cyclopropyl-4-oxo-1,4-dihydro-naphthyridin-3-carbonsaeuren, verfahren zu ihrer herstellung sowie diese enthaltende antibakterielle mittel
DE1802961A1 (de)	1969-05-22	Chromonverbindungen und Verfahren zur Herstellung derselben
CH636839A5 (de)	1983-06-30	4-(2-oxo-1-cycloalkylidenmethyl)-phenylessigsaeurederivate, sowie verfahren zu deren herstellung und pharmazeutisch zulaessige salze solcher verbindungen.
DE2941869C2 (fr)	1988-07-21
EP0064027B1 (fr)	1985-05-22	Dérivés de benzodioxolanes, procédé pour leur préparation et compositions pharmaceutiques les contenant
AT390054B (de)	1990-03-12	Verfahren zur herstellung von neuen benzoylderivaten von aliphatischen carbonsaeuren
DE2647906C2 (de)	1985-01-31	Aroylphenylindene und Aroylphenylnaphthaline und -hydronaphthaline sowie Verfahren zu ihrer Herstellung
CH642077A5 (de)	1984-03-30	3-fluor-10-piperazino-8-substituierte 10,11-dihydrodibenzo-(b,f)-thiepine, deren saeureadditionssalze, verfahren zur herstellung derselben und diese enthaltende zubereitungen.
DE2546738A1 (de)	1976-10-28	Benzophenonderivate, verfahren zu ihrer herstellung und sie enthaltende pharmazeutische mittel
DE2448438A1 (de)	1975-04-24	2-substituierte und 2,2-disubstituierte eckige klammer auf 1,3-dioxoindanyloxy(oder -thio) eckige klammer zu -alkancarbonsaeuren und verfahren zur herstellung derselben
DE2645865C2 (fr)	1988-07-07
DE3111155A1 (de)	1982-09-30	5,6-dimethyl-pyrrolo (2,3-b)pyridine, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel
DE2646213A1 (de)	1977-05-12	Aroylphenylnaphthaline und verfahren zu ihrer herstellung
DE2610501A1 (de)	1977-09-15	1,4-disubstituierte piperazinverbindungen, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
DE1921049A1 (de)	1969-11-06	Neue organische Verbindungen und Verfahren zu ihrer Herstellung
DE1568848C3 (de)	1975-06-19	Trans-Isomere von Alkenderivaten und Verfahren zu Ihrer Herstellung
DE2600182A1 (de)	1976-07-08	Psychotrop und antimikrobiell wirksame polysubstituierte 10-piperazinodibenzo (b,f) thiepinderivate
DE3016616C2 (de)	1982-09-16	2-(6-Methoxy-2-naphthyl)-propylönanthat, Verfahren zu seiner Herstellung und diese enthaltende Arzneimittel
EP0107623A1 (fr)	1984-05-02	Dérivés de benzodioxolanes, leur procédé de préparation et compositions pharmaceutiques les contenant
DE2163908C3 (de)	1977-03-10	2-Aminomethylphenolderivate deren nichtgiftige, pharmazeutisch verwertbare Säureadditionssalze, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende pharmazeutische Mittel Merck & Co., Inc., Rahway, N.J. (V.St.A.)