DE3030323A1 - Die verwendung von imidazolderivaten als spermatostatika oder spermizide - Google Patents
Die verwendung von imidazolderivaten als spermatostatika oder spermizideInfo
- Publication number
- DE3030323A1 DE3030323A1 DE19803030323 DE3030323A DE3030323A1 DE 3030323 A1 DE3030323 A1 DE 3030323A1 DE 19803030323 DE19803030323 DE 19803030323 DE 3030323 A DE3030323 A DE 3030323A DE 3030323 A1 DE3030323 A1 DE 3030323A1
- Authority
- DE
- Germany
- Prior art keywords
- imidazole
- oxalate
- group
- substituted phenyl
- alkyl
- 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.)
- Granted
Links
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 title abstract description 17
- 241000124008 Mammalia Species 0.000 title abstract description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 20
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 15
- 239000002253 acid Substances 0.000 claims abstract description 13
- 150000003839 salts Chemical class 0.000 claims abstract description 13
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 3
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 3
- -1 3-n-octylthio-n-octyl Chemical group 0.000 claims description 49
- 150000001875 compounds Chemical class 0.000 claims description 35
- 239000004480 active ingredient Substances 0.000 claims description 27
- 238000002360 preparation method Methods 0.000 claims description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 230000003315 spermatostatic effect Effects 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 6
- 239000003433 contraceptive agent Substances 0.000 claims description 5
- 230000002254 contraceptive effect Effects 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 4
- 230000037396 body weight Effects 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims description 2
- CLEDFOUEAGECMZ-UHFFFAOYSA-N 1-[2-[(2,4-dichlorophenyl)methoxy]octyl]imidazole;oxalic acid Chemical compound OC(=O)C(O)=O.C=1C=C(Cl)C=C(Cl)C=1COC(CCCCCC)CN1C=CN=C1 CLEDFOUEAGECMZ-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- GWMKCWHBDUFJIT-UHFFFAOYSA-N 1-[4-(4-chlorophenyl)-2-(4-chlorophenyl)sulfanylbutyl]imidazole;nitric acid Chemical compound O[N+]([O-])=O.C1=CC(Cl)=CC=C1CCC(SC=1C=CC(Cl)=CC=1)CN1C=NC=C1 GWMKCWHBDUFJIT-UHFFFAOYSA-N 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 230000003313 weakening effect Effects 0.000 claims 1
- 150000002460 imidazoles Chemical class 0.000 abstract description 2
- DLNLYNRDIKIJAX-UHFFFAOYSA-N 1-[2-[(2-chlorothiophen-3-yl)methylsulfanyl]-2-(2,4-dichlorophenyl)ethyl]imidazole Chemical compound S1C=CC(CSC(CN2C=NC=C2)C=2C(=CC(Cl)=CC=2)Cl)=C1Cl DLNLYNRDIKIJAX-UHFFFAOYSA-N 0.000 abstract 1
- GNZHVEIGGFMLSP-UHFFFAOYSA-N 1-[[2-(2,4-dichlorophenyl)-4-[(4-phenylphenoxy)methyl]-1,3-dioxolan-2-yl]methyl]imidazole Chemical compound ClC1=CC(Cl)=CC=C1C1(CN2C=NC=C2)OC(COC=2C=CC(=CC=2)C=2C=CC=CC=2)CO1 GNZHVEIGGFMLSP-UHFFFAOYSA-N 0.000 abstract 1
- XMAYWYJOQHXEEK-UHFFFAOYSA-N 1-acetyl-4-(4-{[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazine Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1OCC1OC(CN2C=NC=C2)(C=2C(=CC(Cl)=CC=2)Cl)OC1 XMAYWYJOQHXEEK-UHFFFAOYSA-N 0.000 abstract 1
- QXHHHPZILQDDPS-UHFFFAOYSA-N 1-{2-[(2-chloro-3-thienyl)methoxy]-2-(2,4-dichlorophenyl)ethyl}imidazole Chemical compound S1C=CC(COC(CN2C=NC=C2)C=2C(=CC(Cl)=CC=2)Cl)=C1Cl QXHHHPZILQDDPS-UHFFFAOYSA-N 0.000 abstract 1
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
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- 241000282472 Canis lupus familiaris Species 0.000 description 4
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- 239000000839 emulsion Substances 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
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- 235000019359 magnesium stearate Nutrition 0.000 description 4
- 229940057948 magnesium stearate Drugs 0.000 description 4
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- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 4
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- GPUZWNNASIXLTQ-UHFFFAOYSA-N 1h-imidazole;oxalic acid Chemical compound C1=CNC=N1.OC(=O)C(O)=O GPUZWNNASIXLTQ-UHFFFAOYSA-N 0.000 description 3
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- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
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- 229920001615 Tragacanth Polymers 0.000 description 1
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- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
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- 229960004543 anhydrous citric acid Drugs 0.000 description 1
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- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 1
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- 239000012458 free base Substances 0.000 description 1
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- 239000007903 gelatin capsule Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- UBHWBODXJBSFLH-UHFFFAOYSA-N hexadecan-1-ol;octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO.CCCCCCCCCCCCCCCCCCO UBHWBODXJBSFLH-UHFFFAOYSA-N 0.000 description 1
- 150000002431 hydrogen Chemical group 0.000 description 1
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- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
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- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
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- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
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- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
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- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
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- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229940113116 polyethylene glycol 1000 Drugs 0.000 description 1
- 229940068918 polyethylene glycol 400 Drugs 0.000 description 1
- 229940057838 polyethylene glycol 4000 Drugs 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 229940068965 polysorbates Drugs 0.000 description 1
- 229920006316 polyvinylpyrrolidine Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 235000020183 skimmed milk Nutrition 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
- 239000001587 sorbitan monostearate Substances 0.000 description 1
- 235000011076 sorbitan monostearate Nutrition 0.000 description 1
- 229940035048 sorbitan monostearate Drugs 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000000934 spermatocidal agent Substances 0.000 description 1
- 230000001150 spermicidal effect Effects 0.000 description 1
- 239000011493 spray foam Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
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- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- OULAJFUGPPVRBK-UHFFFAOYSA-N tetratriacontyl alcohol Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO OULAJFUGPPVRBK-UHFFFAOYSA-N 0.000 description 1
- 210000001215 vagina Anatomy 0.000 description 1
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- 239000000286 vaginal jelly Substances 0.000 description 1
- 229940120293 vaginal suppository Drugs 0.000 description 1
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- 235000013311 vegetables Nutrition 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19803030323 DE3030323A1 (de) | 1980-08-11 | 1980-08-11 | Die verwendung von imidazolderivaten als spermatostatika oder spermizide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19803030323 DE3030323A1 (de) | 1980-08-11 | 1980-08-11 | Die verwendung von imidazolderivaten als spermatostatika oder spermizide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3030323A1 true DE3030323A1 (de) | 1982-03-11 |
| DE3030323C2 DE3030323C2 (enExample) | 1990-07-12 |
Family
ID=6109367
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19803030323 Granted DE3030323A1 (de) | 1980-08-11 | 1980-08-11 | Die verwendung von imidazolderivaten als spermatostatika oder spermizide |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE3030323A1 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0070525A3 (en) * | 1981-07-22 | 1984-01-11 | Toko Yakuhin Industry Co., Ltd. | Pharmaceutical preparations for external use |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4078071A (en) * | 1976-03-08 | 1978-03-07 | Syntex (U.S.A.) Inc. | Derivatives of substituted N-alkyl imidazoles |
-
1980
- 1980-08-11 DE DE19803030323 patent/DE3030323A1/de active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4078071A (en) * | 1976-03-08 | 1978-03-07 | Syntex (U.S.A.) Inc. | Derivatives of substituted N-alkyl imidazoles |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0070525A3 (en) * | 1981-07-22 | 1984-01-11 | Toko Yakuhin Industry Co., Ltd. | Pharmaceutical preparations for external use |
Also Published As
| Publication number | Publication date |
|---|---|
| DE3030323C2 (enExample) | 1990-07-12 |
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| Date | Code | Title | Description |
|---|---|---|---|
| 8101 | Request for examination as to novelty | ||
| 8105 | Search report available | ||
| 8110 | Request for examination paragraph 44 | ||
| 8128 | New person/name/address of the agent |
Representative=s name: DANNENBERG, G., DIPL.-ING., 6000 FRANKFURT WEINHOL |
|
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |