NL7907317A - Contraceptiemiddel voor mannen. - Google Patents

Contraceptiemiddel voor mannen. Download PDF

Info

Publication number: NL7907317A
Authority: NL; Netherlands
Prior art keywords: compound; compound according; methoxy; methyl; formula
Prior art date: 1978-10-10

Application number

NL7907317A

Other languages

English (en)

Dutch (nl)

Original Assignee

Upjohn Co

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.)

1978-10-10

Filing date

1979-10-02

Publication date

1980-04-14

1979-10-02 Application filed by Upjohn Co filed Critical Upjohn Co

1980-04-14 Publication of NL7907317A publication Critical patent/NL7907317A/nl

Links

150000001875 compounds Chemical class 0.000 claims description 257
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 70
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 61
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 51
239000008194 pharmaceutical composition Substances 0.000 claims description 46
241001465754 Metazoa Species 0.000 claims description 41
-1 hydroxy- Chemical class 0.000 claims description 32
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 31
125000004432 carbon atom Chemical group C* 0.000 claims description 30
125000000217 alkyl group Chemical group 0.000 claims description 20
239000005977 Ethylene Substances 0.000 claims description 18
239000002775 capsule Substances 0.000 claims description 18
239000000825 pharmaceutical preparation Substances 0.000 claims description 18
239000001257 hydrogen Substances 0.000 claims description 17
229910052739 hydrogen Inorganic materials 0.000 claims description 17
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
229910052801 chlorine Inorganic materials 0.000 claims description 15
239000000460 chlorine Substances 0.000 claims description 14
125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 14
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 14
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 13
239000011737 fluorine Substances 0.000 claims description 13
229910052731 fluorine Inorganic materials 0.000 claims description 13
239000000725 suspension Substances 0.000 claims description 13
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 12
239000007788 liquid Substances 0.000 claims description 10
150000002923 oximes Chemical class 0.000 claims description 10
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 9
125000003342 alkenyl group Chemical group 0.000 claims description 9
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 9
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 7
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 7
235000009508 confectionery Nutrition 0.000 claims description 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
229910052717 sulfur Inorganic materials 0.000 claims description 6
125000004434 sulfur atom Chemical group 0.000 claims description 6
239000006188 syrup Substances 0.000 claims description 6
235000020357 syrup Nutrition 0.000 claims description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 5
150000004292 cyclic ethers Chemical class 0.000 claims description 5
125000000304 alkynyl group Chemical group 0.000 claims description 4
125000004356 hydroxy functional group Chemical group O* 0.000 claims description 4
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
229910052794 bromium Inorganic materials 0.000 claims description 3
229910052799 carbon Inorganic materials 0.000 claims description 3
239000003937 drug carrier Substances 0.000 claims description 3
239000000839 emulsion Substances 0.000 claims description 3
125000001153 fluoro group Chemical group F* 0.000 claims description 3
229910052760 oxygen Inorganic materials 0.000 claims description 3
239000001301 oxygen Substances 0.000 claims description 3
125000004430 oxygen atom Chemical group O* 0.000 claims description 3
MSEZLHAVPJYYIQ-VMXHOPILSA-N (8s,9s,10r,13s,14s)-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CCC[C@@]1(C)CC2 MSEZLHAVPJYYIQ-VMXHOPILSA-N 0.000 claims description 2
125000003277 amino group Chemical group 0.000 claims description 2
125000004429 atom Chemical group 0.000 claims description 2
239000000463 material Substances 0.000 claims description 2
WEMHXCDJLLUKDN-APYPKHJSSA-N (2R,5S,8R,9S,10S,13S,14S,17S)-2-chloro-17-methoxy-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one Chemical compound C([C@@H]1CC2)C(=O)[C@H](Cl)C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H](OC)[C@@]2(C)CC1 WEMHXCDJLLUKDN-APYPKHJSSA-N 0.000 claims 1
HUTPASNYCBFLJN-NWIDBOESSA-N (5S,8R,9S,10S,13S,14S)-17-heptoxy-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one Chemical compound C(CCCCCC)OC1[C@]2(C)[C@@H](CC1)[C@@H]1CC[C@H]3CC(CC[C@]3(C)[C@H]1CC2)=O HUTPASNYCBFLJN-NWIDBOESSA-N 0.000 claims 1
241001516584 Andrya Species 0.000 claims 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 1
125000001246 bromo group Chemical group Br* 0.000 claims 1
229910052698 phosphorus Inorganic materials 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 137
239000000203 mixture Substances 0.000 description 113
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 84
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 69
150000003431 steroids Chemical class 0.000 description 60
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 58
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 47
238000000034 method Methods 0.000 description 41
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 38
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 30
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
239000002583 male contraceptive agent Substances 0.000 description 26
238000007429 general method Methods 0.000 description 24
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 23
239000000741 silica gel Substances 0.000 description 23
229910002027 silica gel Inorganic materials 0.000 description 23
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 22
239000003826 tablet Substances 0.000 description 22
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 20
239000002480 mineral oil Substances 0.000 description 19
235000010446 mineral oil Nutrition 0.000 description 19
239000000047 product Substances 0.000 description 19
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 16
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
239000003433 contraceptive agent Substances 0.000 description 16
239000007787 solid Substances 0.000 description 16
239000000243 solution Substances 0.000 description 16
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
238000006243 chemical reaction Methods 0.000 description 14
238000002360 preparation method Methods 0.000 description 14
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 12
239000002552 dosage form Substances 0.000 description 12
150000002170 ethers Chemical class 0.000 description 12
239000000706 filtrate Substances 0.000 description 12
239000002244 precipitate Substances 0.000 description 12
238000010992 reflux Methods 0.000 description 12
239000002002 slurry Substances 0.000 description 12
241000282472 Canis lupus familiaris Species 0.000 description 11
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 11
239000000126 substance Substances 0.000 description 11
VMNRNUNYBVFVQI-QYXZOKGRSA-N (5s,8s,9s,10s,13s,14s)-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one Chemical compound C([C@@H]1CC2)C(=O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CCC[C@@]2(C)CC1 VMNRNUNYBVFVQI-QYXZOKGRSA-N 0.000 description 10
230000002254 contraceptive effect Effects 0.000 description 10
SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical group OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 description 10
NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 10
239000003085 diluting agent Substances 0.000 description 9
229910052757 nitrogen Inorganic materials 0.000 description 9
239000011541 reaction mixture Substances 0.000 description 9
241000283984 Rodentia Species 0.000 description 8
239000004480 active ingredient Substances 0.000 description 8
230000001568 sexual effect Effects 0.000 description 8
238000003756 stirring Methods 0.000 description 8
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 7
230000002441 reversible effect Effects 0.000 description 7
229910052938 sodium sulfate Inorganic materials 0.000 description 7
235000011152 sodium sulphate Nutrition 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
150000001441 androstanes Chemical class 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 6
239000012267 brine Substances 0.000 description 6
239000007891 compressed tablet Substances 0.000 description 6
235000013305 food Nutrition 0.000 description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
208000021267 infertility disease Diseases 0.000 description 6
239000010410 layer Substances 0.000 description 6
239000012074 organic phase Substances 0.000 description 6
239000000843 powder Substances 0.000 description 6
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 6
ROVSAVJEBQAVFO-PFFQMSPKSA-N (5s,8s,9s,10s,13s,14s)-10,13-dimethyl-1,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-2-one Chemical compound C([C@@H]1CC2)CC(=O)C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CCC[C@@]2(C)CC1 ROVSAVJEBQAVFO-PFFQMSPKSA-N 0.000 description 5
101150041968 CDC13 gene Proteins 0.000 description 5
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 5
YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 5
241000282326 Felis catus Species 0.000 description 5
241000700159 Rattus Species 0.000 description 5
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 5
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 5
239000002585 base Substances 0.000 description 5
244000309464 bull Species 0.000 description 5
229940124558 contraceptive agent Drugs 0.000 description 5
239000000796 flavoring agent Substances 0.000 description 5
235000019634 flavors Nutrition 0.000 description 5
238000010438 heat treatment Methods 0.000 description 5
238000004519 manufacturing process Methods 0.000 description 5
229910001923 silver oxide Inorganic materials 0.000 description 5
125000001424 substituent group Chemical group 0.000 description 5
238000003786 synthesis reaction Methods 0.000 description 5
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 4
QZLYKIGBANMMBK-UGCZWRCOSA-N 5α-Androstane Chemical compound C([C@@H]1CC2)CCC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CCC[C@@]2(C)CC1 QZLYKIGBANMMBK-UGCZWRCOSA-N 0.000 description 4
KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 4
108010010803 Gelatin Proteins 0.000 description 4
241000124008 Mammalia Species 0.000 description 4
241000699666 Mus <mouse, genus> Species 0.000 description 4
JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 4
229920002472 Starch Polymers 0.000 description 4
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 4
229930006000 Sucrose Natural products 0.000 description 4
MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testostosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
238000000576 coating method Methods 0.000 description 4
239000012043 crude product Substances 0.000 description 4
239000000975 dye Substances 0.000 description 4
230000000694 effects Effects 0.000 description 4
230000012173 estrus Effects 0.000 description 4
IIEWJVIFRVWJOD-UHFFFAOYSA-N ethyl cyclohexane Natural products CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 4
239000000284 extract Substances 0.000 description 4
229920000159 gelatin Polymers 0.000 description 4
239000008273 gelatin Substances 0.000 description 4
235000019322 gelatine Nutrition 0.000 description 4
235000011852 gelatine desserts Nutrition 0.000 description 4
150000004820 halides Chemical class 0.000 description 4
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 4
210000004185 liver Anatomy 0.000 description 4
238000002156 mixing Methods 0.000 description 4
235000019698 starch Nutrition 0.000 description 4
239000008107 starch Substances 0.000 description 4
239000005720 sucrose Substances 0.000 description 4
YUKQRDCYNOVPGJ-UHFFFAOYSA-N thioacetamide Chemical compound CC(N)=S YUKQRDCYNOVPGJ-UHFFFAOYSA-N 0.000 description 4
DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 4
239000001993 wax Substances 0.000 description 4
HUHXLHLWASNVDB-UHFFFAOYSA-N 2-(oxan-2-yloxy)oxane Chemical class O1CCCCC1OC1OCCCC1 HUHXLHLWASNVDB-UHFFFAOYSA-N 0.000 description 3
235000019739 Dicalciumphosphate Nutrition 0.000 description 3
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
240000004808 Saccharomyces cerevisiae Species 0.000 description 3
235000014680 Saccharomyces cerevisiae Nutrition 0.000 description 3
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 3
208000031271 Unwanted pregnancy Diseases 0.000 description 3
230000003509 anti-fertility effect Effects 0.000 description 3
239000011230 binding agent Substances 0.000 description 3
239000001506 calcium phosphate Substances 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
239000003153 chemical reaction reagent Substances 0.000 description 3
238000004440 column chromatography Methods 0.000 description 3
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239000012141 concentrate Substances 0.000 description 3
238000001816 cooling Methods 0.000 description 3
NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 3
229910000390 dicalcium phosphate Inorganic materials 0.000 description 3
229940038472 dicalcium phosphate Drugs 0.000 description 3
235000005911 diet Nutrition 0.000 description 3
230000037213 diet Effects 0.000 description 3
150000002118 epoxides Chemical class 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
239000003925 fat Substances 0.000 description 3
235000003599 food sweetener Nutrition 0.000 description 3
HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
229910052943 magnesium sulfate Inorganic materials 0.000 description 3
235000019341 magnesium sulphate Nutrition 0.000 description 3
HDZGCSFEDULWCS-UHFFFAOYSA-N monomethylhydrazine Chemical compound CNN HDZGCSFEDULWCS-UHFFFAOYSA-N 0.000 description 3
HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 3
229940067157 phenylhydrazine Drugs 0.000 description 3
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 3
108090000623 proteins and genes Proteins 0.000 description 3
102000004169 proteins and genes Human genes 0.000 description 3
150000003217 pyrazoles Chemical class 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
239000001632 sodium acetate Substances 0.000 description 3
235000017281 sodium acetate Nutrition 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
239000012279 sodium borohydride Substances 0.000 description 3
229910000033 sodium borohydride Inorganic materials 0.000 description 3
230000003637 steroidlike Effects 0.000 description 3
239000003765 sweetening agent Substances 0.000 description 3
239000000454 talc Substances 0.000 description 3
229910052623 talc Inorganic materials 0.000 description 3
235000012222 talc Nutrition 0.000 description 3
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
238000005406 washing Methods 0.000 description 3
239000010497 wheat germ oil Substances 0.000 description 3
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238000004949 mass spectrometry Methods 0.000 description 1
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150000002905 orthoesters Chemical class 0.000 description 1
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239000008024 pharmaceutical diluent Substances 0.000 description 1
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125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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150000003242 quaternary ammonium salts Chemical class 0.000 description 1
DCBSHORRWZKAKO-UHFFFAOYSA-N rac-1-monomyristoylglycerol Chemical compound CCCCCCCCCCCCCC(=O)OCC(O)CO DCBSHORRWZKAKO-UHFFFAOYSA-N 0.000 description 1
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CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
229940081974 saccharin Drugs 0.000 description 1
235000019204 saccharin Nutrition 0.000 description 1
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150000003333 secondary alcohols Chemical class 0.000 description 1
210000000582 semen Anatomy 0.000 description 1
210000001625 seminal vesicle Anatomy 0.000 description 1
230000035807 sensation Effects 0.000 description 1
235000019615 sensations Nutrition 0.000 description 1
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
229960001462 sodium cyclamate Drugs 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
239000002904 solvent Substances 0.000 description 1
230000000920 spermatogeneic effect Effects 0.000 description 1
239000007921 spray Substances 0.000 description 1
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230000001954 sterilising effect Effects 0.000 description 1
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210000002784 stomach Anatomy 0.000 description 1
FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 1
125000001650 tertiary alcohol group Chemical group 0.000 description 1
150000003509 tertiary alcohols Chemical class 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
- C07J71/0073—Sulfur-containing hetero ring
- C07J71/0078—Sulfur-containing hetero ring containing only sulfur
- C07J71/0084—Episulfides
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
- C07J1/0003—Androstane derivatives
- C07J1/0018—Androstane derivatives substituted in position 17 beta, not substituted in position 17 alfa
- C07J1/0022—Androstane derivatives substituted in position 17 beta, not substituted in position 17 alfa the substituent being an OH group free esterified or etherified
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
- C07J1/0003—Androstane derivatives
- C07J1/0018—Androstane derivatives substituted in position 17 beta, not substituted in position 17 alfa
- C07J1/0022—Androstane derivatives substituted in position 17 beta, not substituted in position 17 alfa the substituent being an OH group free esterified or etherified
- C07J1/0029—Ethers
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
- C07J1/0003—Androstane derivatives
- C07J1/0033—Androstane derivatives substituted in position 17 alfa and 17 beta
- C07J1/0037—Androstane derivatives substituted in position 17 alfa and 17 beta the substituent in position 17 alfa being a saturated hydrocarbon group
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
- C07J1/0003—Androstane derivatives
- C07J1/0033—Androstane derivatives substituted in position 17 alfa and 17 beta
- C07J1/004—Androstane derivatives substituted in position 17 alfa and 17 beta the substituent in position 17 alfa being an unsaturated hydrocarbon group
- C07J1/0048—Alkynyl derivatives
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J21/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having an oxygen-containing hetero ring spiro-condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J21/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having an oxygen-containing hetero ring spiro-condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C07J21/005—Ketals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J21/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having an oxygen-containing hetero ring spiro-condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C07J21/005—Ketals
- C07J21/006—Ketals at position 3
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
- C07J41/0005—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring the nitrogen atom being directly linked to the cyclopenta(a)hydro phenanthrene skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
- C07J41/0005—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring the nitrogen atom being directly linked to the cyclopenta(a)hydro phenanthrene skeleton
- C07J41/0016—Oximes
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J53/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by condensation with a carbocyclic rings or by formation of an additional ring by means of a direct link between two ring carbon atoms, including carboxyclic rings fused to the cyclopenta(a)hydrophenanthrene skeleton are included in this class
- C07J53/001—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by condensation with a carbocyclic rings or by formation of an additional ring by means of a direct link between two ring carbon atoms, including carboxyclic rings fused to the cyclopenta(a)hydrophenanthrene skeleton are included in this class spiro-linked
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J53/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by condensation with a carbocyclic rings or by formation of an additional ring by means of a direct link between two ring carbon atoms, including carboxyclic rings fused to the cyclopenta(a)hydrophenanthrene skeleton are included in this class
- C07J53/002—Carbocyclic rings fused
- C07J53/004—3 membered carbocyclic rings
- C07J53/005—3 membered carbocyclic rings in position 12
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
- C07J71/0005—Oxygen-containing hetero ring
- C07J71/001—Oxiranes
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
- C07J71/0036—Nitrogen-containing hetero ring
- C07J71/0042—Nitrogen only
- C07J71/0047—Nitrogen only at position 2(3)
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
- C07J71/0036—Nitrogen-containing hetero ring
- C07J71/0057—Nitrogen and oxygen
- C07J71/0063—Nitrogen and oxygen at position 2(3)
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
- C07J71/0073—Sulfur-containing hetero ring
- C07J71/0094—Sulfur-containing hetero ring containing sulfur and nitrogen

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Steroid Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

NL7907317A 1978-10-10 1979-10-02 Contraceptiemiddel voor mannen. NL7907317A (nl)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US05/949,797 US4297350A (en)	1978-10-10	1978-10-10	Male contraceptive steroids and methods of use
US94979778		1978-10-10

Publications (1)

Publication Number	Publication Date
NL7907317A true NL7907317A (nl)	1980-04-14

Family

ID=25489549

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL7907317A NL7907317A (nl)	1978-10-10	1979-10-02	Contraceptiemiddel voor mannen.

Country Status (8)

Country	Link
US (1)	US4297350A (de)
JP (1)	JPS5555200A (de)
CH (1)	CH643565A5 (de)
DE (1)	DE2940132A1 (de)
FR (1)	FR2438663A1 (de)
GB (1)	GB2032924B (de)
IT (1)	IT1124568B (de)
NL (1)	NL7907317A (de)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4684636A (en) *	1985-06-24	1987-08-04	Sterling Drug Inc.	Antiandrogenic sulfonylsteroidopyrazoles and processes for preparation method of use and compositions thereof
US5134135A (en) *	1990-06-21	1992-07-28	Sterling Drug Inc.	Antiandrogenic sulfonylsteroidooxazoles
DE4021433A1 (de) *	1990-07-04	1992-01-09	Schering Ag	Antiandrogene mit steroid(3,2-c)pyrazol-struktur
AU2769092A (en) *	1991-10-23	1993-05-21	Akzo Nobel N.V.	Pest control compositions
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1978
- 1978-10-10 US US05/949,797 patent/US4297350A/en not_active Expired - Lifetime
1979
- 1979-10-02 NL NL7907317A patent/NL7907317A/nl not_active Application Discontinuation
- 1979-10-02 GB GB7934064A patent/GB2032924B/en not_active Expired
- 1979-10-03 DE DE19792940132 patent/DE2940132A1/de not_active Ceased
- 1979-10-04 IT IT26267/79A patent/IT1124568B/it active
- 1979-10-09 FR FR7925102A patent/FR2438663A1/fr active Granted
- 1979-10-10 CH CH911679A patent/CH643565A5/de not_active IP Right Cessation
- 1979-10-11 JP JP13126279A patent/JPS5555200A/ja active Pending

Also Published As

Publication number	Publication date
FR2438663A1 (fr)	1980-05-09
US4297350A (en)	1981-10-27
GB2032924B (en)	1982-12-22
IT7926267A0 (it)	1979-10-04
JPS5555200A (en)	1980-04-22
GB2032924A (en)	1980-05-14
FR2438663B1 (de)	1983-06-03
CH643565A5 (de)	1984-06-15
DE2940132A1 (de)	1980-04-24
IT1124568B (it)	1986-05-07

Legal Events

Date	Code	Title
1985-01-01	A85	Still pending on 85-01-01
1986-09-01	BA	A request for search or an international-type search has been filed
1986-10-01	BB	A search report has been drawn up
1986-11-03	BC	A request for examination has been filed
1990-06-01	BV	The patent application has lapsed

Publication	Publication Date	Title
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US4160027A (en)	1979-07-03	Steroid cyanoketones and intermediates
JP2000503980A (ja)	2000-04-04	新規１９―ノル−プレグネン誘導体類
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JP2000256390A (ja)	2000-09-19	性ステロイド活性を抑制するために用いるエストロゲン核誘導体の医薬組成物
US4297350A (en)	1981-10-27	Male contraceptive steroids and methods of use
DE69910068T2 (de)	2004-04-15	17beta-acyl-17alpha-propynyl-11beta-arylsteroide und ihre derivate mit agonistischen oder antagonistischen hormonalen aktivitäten
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US3200114A (en)	1965-08-10	17-tetrahydropyranyl ethers of (3, 2-c)-pyrazole and (2, 3-d)-isoxazole derivatives o the androstane and 19-norandrostane series
US3980638A (en)	1976-09-14	Testosterone derivatives
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RU2683953C1 (ru)	2019-04-03	17α-АЦЕТОКСИ-3β-ГЕКСАНОИЛОКСИ-6-МЕТИЛПРЕГНА-4,6-ДИЕН-20-ОН, ОБЛАДАЮЩИЙ ГЕСТАГЕННОЙ, КОНТРАЦЕПТИВНОЙ И ПРОТИВООПУХОЛЕВОЙ АКТИВНОСТЬЮ, И СПОСОБ ЕГО ПОЛУЧЕНИЯ
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DE19961219A1 (de)	2001-07-19	11beta-Phenylestratrien-Derivate mit Fluoralkylgruppen in der aromatischen Seitenkette, deren Herstellung und diese Verbindungen enthaltende pharmazeutische Zusammensetzungen
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