AU605522B2 - Carboxamido ethyl-imidazole and-1,2,4-triazole derivatives - Google Patents

Carboxamido ethyl-imidazole and-1,2,4-triazole derivatives Download PDF

Info

Publication number: AU605522B2
Authority: AU; Australia
Prior art keywords: halogen; substituted; compound; cyano; heteroaryl
Prior art date: 1986-12-03
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.): Ceased

Application number

AU81962/87A

Other languages

English (en)

Other versions

AU8196287A (en

Inventor

Helmut Egger

Rudolf Walchli

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Sandoz AG

Original Assignee

Sandoz AG

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.)

1986-12-03

Filing date

1987-12-01

Publication date

1991-01-17

1987-12-01 Application filed by Sandoz AG filed Critical Sandoz AG

1988-06-16 Publication of AU8196287A publication Critical patent/AU8196287A/en

1991-01-17 Application granted granted Critical

1991-01-17 Publication of AU605522B2 publication Critical patent/AU605522B2/en

2007-12-01 Anticipated expiration legal-status Critical

Status Ceased legal-status Critical Current

Links

-1 Carboxamido ethyl-imidazole Chemical compound 0.000 title claims description 7
JDIPHBYZUMQFQV-UHFFFAOYSA-N 5-ethyl-1h-1,2,4-triazole Chemical class CCC1=NC=NN1 JDIPHBYZUMQFQV-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 26
125000004093 cyano group Chemical group *C#N 0.000 claims description 16
229910052736 halogen Inorganic materials 0.000 claims description 16
125000001072 heteroaryl group Chemical group 0.000 claims description 16
239000002253 acid Substances 0.000 claims description 14
125000003118 aryl group Chemical group 0.000 claims description 14
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
150000003839 salts Chemical group 0.000 claims description 13
125000000217 alkyl group Chemical group 0.000 claims description 11
150000002367 halogens Chemical class 0.000 claims description 11
125000003545 alkoxy group Chemical group 0.000 claims description 9
125000005843 halogen group Chemical group 0.000 claims description 7
238000000034 method Methods 0.000 claims description 7
239000004721 Polyphenylene oxide Chemical group 0.000 claims description 5
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 5
125000000753 cycloalkyl group Chemical group 0.000 claims description 5
229920000570 polyether Chemical group 0.000 claims description 5
150000003431 steroids Chemical class 0.000 claims description 5
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 5
206010028980 Neoplasm Diseases 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
230000001419 dependent effect Effects 0.000 claims description 3
239000008194 pharmaceutical composition Substances 0.000 claims description 3
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
239000005864 Sulphur Substances 0.000 claims description 2
125000005842 heteroatom Chemical group 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
125000006413 ring segment Chemical group 0.000 claims description 2
125000006705 (C5-C7) cycloalkyl group Chemical group 0.000 claims 1
239000003085 diluting agent Substances 0.000 claims 1
LONWTLLIALIPKY-UHFFFAOYSA-N n-[2,2-bis(4-chlorophenyl)-2-imidazol-1-ylethyl]-4-chlorobenzamide Chemical compound C1=CC(Cl)=CC=C1C(=O)NCC(N1C=NC=C1)(C=1C=CC(Cl)=CC=1)C1=CC=C(Cl)C=C1 LONWTLLIALIPKY-UHFFFAOYSA-N 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
239000000243 solution Substances 0.000 description 10
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
230000000694 effects Effects 0.000 description 7
238000012360 testing method Methods 0.000 description 7
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
241000700159 Rattus Species 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
210000001672 ovary Anatomy 0.000 description 5
239000000126 substance Substances 0.000 description 5
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 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
230000010933 acylation Effects 0.000 description 4
238000005917 acylation reaction Methods 0.000 description 4
239000008280 blood Substances 0.000 description 4
210000004369 blood Anatomy 0.000 description 4
125000004432 carbon atom Chemical group C* 0.000 description 4
238000001816 cooling Methods 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
125000001424 substituent group Chemical group 0.000 description 4
VOXZDWNPVJITMN-ZBRFXRBCSA-N 17β-estradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 VOXZDWNPVJITMN-ZBRFXRBCSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
239000008346 aqueous phase Substances 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
229930182833 estradiol Natural products 0.000 description 3
239000000262 estrogen Substances 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
239000011737 fluorine Substances 0.000 description 3
229910052731 fluorine Inorganic materials 0.000 description 3
239000012458 free base Substances 0.000 description 3
230000005764 inhibitory process Effects 0.000 description 3
229910052943 magnesium sulfate Inorganic materials 0.000 description 3
235000019341 magnesium sulphate Nutrition 0.000 description 3
210000001589 microsome Anatomy 0.000 description 3
239000000203 mixture Substances 0.000 description 3
125000000896 monocarboxylic acid group Chemical group 0.000 description 3
230000016087 ovulation Effects 0.000 description 3
239000000047 product Substances 0.000 description 3
239000007858 starting material Substances 0.000 description 3
210000004291 uterus Anatomy 0.000 description 3
JKANPLQGHAPMHN-UHFFFAOYSA-N 2,2-bis(4-chlorophenyl)-2-imidazol-1-ylethanamine Chemical compound ClC1=CC=C(C=C1)C(CN)(N1C=NC=C1)C1=CC=C(C=C1)Cl JKANPLQGHAPMHN-UHFFFAOYSA-N 0.000 description 2
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
102000014654 Aromatase Human genes 0.000 description 2
108010078554 Aromatase Proteins 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
DNXHEGUUPJUMQT-CBZIJGRNSA-N Estrone Chemical compound OC1=CC=C2[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 DNXHEGUUPJUMQT-CBZIJGRNSA-N 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
239000007983 Tris buffer Substances 0.000 description 2
229960005471 androstenedione Drugs 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
229960004132 diethyl ether Drugs 0.000 description 2
239000003814 drug Substances 0.000 description 2
239000003112 inhibitor Substances 0.000 description 2
210000000056 organ Anatomy 0.000 description 2
239000003208 petroleum Substances 0.000 description 2
210000002826 placenta Anatomy 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
239000002904 solvent Substances 0.000 description 2
229960003604 testosterone Drugs 0.000 description 2
150000003852 triazoles Chemical class 0.000 description 2
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 2
DNXHEGUUPJUMQT-UHFFFAOYSA-N (+)-estrone Natural products OC1=CC=C2C3CCC(C)(C(CC4)=O)C4C3CCC2=C1 DNXHEGUUPJUMQT-UHFFFAOYSA-N 0.000 description 1
ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 1
QNVFPSWLFFTNNU-UHFFFAOYSA-N 2,2-bis(4-chlorophenyl)aziridine Chemical compound C1=CC(Cl)=CC=C1C1(C=2C=CC(Cl)=CC=2)NC1 QNVFPSWLFFTNNU-UHFFFAOYSA-N 0.000 description 1
PQAMFDRRWURCFQ-UHFFFAOYSA-N 2-ethyl-1h-imidazole Chemical compound CCC1=NC=CN1 PQAMFDRRWURCFQ-UHFFFAOYSA-N 0.000 description 1
KPUFKAJHUNSWGV-UHFFFAOYSA-N 2-imidazol-1-yl-2,2-diphenylethanamine Chemical compound C1(=CC=CC=C1)C(CN)(N1C=NC=C1)C1=CC=CC=C1 KPUFKAJHUNSWGV-UHFFFAOYSA-N 0.000 description 1
RKIDDEGICSMIJA-UHFFFAOYSA-N 4-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C=C1 RKIDDEGICSMIJA-UHFFFAOYSA-N 0.000 description 1
KYARBIJYVGJZLB-UHFFFAOYSA-N 7-amino-4-hydroxy-2-naphthalenesulfonic acid Chemical compound OC1=CC(S(O)(=O)=O)=CC2=CC(N)=CC=C21 KYARBIJYVGJZLB-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 1
208000026310 Breast neoplasm Diseases 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
101150041968 CDC13 gene Proteins 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
201000009030 Carcinoma Diseases 0.000 description 1
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
108090000790 Enzymes Proteins 0.000 description 1
102000004190 Enzymes Human genes 0.000 description 1
241001326189 Gyrodactylus prostae Species 0.000 description 1
206010020880 Hypertrophy Diseases 0.000 description 1
101000913968 Ipomoea purpurea Chalcone synthase C Proteins 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
101710162501 Ovarian aromatase Proteins 0.000 description 1
241001610364 Ovula Species 0.000 description 1
101000907988 Petunia hybrida Chalcone-flavanone isomerase C Proteins 0.000 description 1
206010036049 Polycystic ovaries Diseases 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
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 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
PDMMFKSKQVNJMI-BLQWBTBKSA-N Testosterone propionate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](OC(=O)CC)[C@@]1(C)CC2 PDMMFKSKQVNJMI-BLQWBTBKSA-N 0.000 description 1
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
210000004100 adrenal gland Anatomy 0.000 description 1
125000003342 alkenyl group Chemical group 0.000 description 1
125000000304 alkynyl group Chemical group 0.000 description 1
230000004075 alteration Effects 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
239000003886 aromatase inhibitor Substances 0.000 description 1
229940046844 aromatase inhibitors Drugs 0.000 description 1
238000005899 aromatization reaction Methods 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
239000002585 base Substances 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000000903 blocking effect Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
210000000481 breast Anatomy 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
239000002775 capsule Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
210000004027 cell Anatomy 0.000 description 1
210000003855 cell nucleus Anatomy 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
230000008859 change Effects 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
230000001684 chronic effect Effects 0.000 description 1
231100000762 chronic effect Toxicity 0.000 description 1
239000013078 crystal Substances 0.000 description 1
230000029087 digestion Effects 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
210000004696 endometrium Anatomy 0.000 description 1
230000002255 enzymatic effect Effects 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
229960003399 estrone Drugs 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
229940088597 hormone Drugs 0.000 description 1
239000005556 hormone Substances 0.000 description 1
NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
125000004130 indan-2-yl group Chemical group [H]C1=C([H])C([H])=C2C(=C1[H])C([H])([H])C([H])(*)C2([H])[H] 0.000 description 1
125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 description 1
231100000546 inhibition of ovulation Toxicity 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000000155 melt Substances 0.000 description 1
210000003470 mitochondria Anatomy 0.000 description 1
238000002156 mixing Methods 0.000 description 1
KAXTWDXRCMICEQ-UHFFFAOYSA-N n-[1-(4-chlorophenyl)ethylidene]hydroxylamine Chemical compound ON=C(C)C1=CC=C(Cl)C=C1 KAXTWDXRCMICEQ-UHFFFAOYSA-N 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
239000008188 pellet Substances 0.000 description 1
239000008024 pharmaceutical diluent Substances 0.000 description 1
239000012071 phase Substances 0.000 description 1
238000005191 phase separation Methods 0.000 description 1
201000010065 polycystic ovary syndrome Diseases 0.000 description 1
230000008569 process Effects 0.000 description 1
210000002307 prostate Anatomy 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000006722 reduction reaction Methods 0.000 description 1
230000001172 regenerating effect Effects 0.000 description 1
238000004062 sedimentation Methods 0.000 description 1
229960004509 serum gonadotrophin Drugs 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
239000000758 substrate Substances 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
239000013589 supplement Substances 0.000 description 1
238000001356 surgical procedure Methods 0.000 description 1
239000000725 suspension Substances 0.000 description 1
208000011580 syndromic disease Diseases 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
229960001712 testosterone propionate Drugs 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
238000011121 vaginal smear Methods 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Urology & Nephrology (AREA)
Endocrinology (AREA)
Reproductive Health (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Plural Heterocyclic Compounds (AREA)

AU81962/87A 1986-12-03 1987-12-01 Carboxamido ethyl-imidazole and-1,2,4-triazole derivatives Ceased AU605522B2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE3641320		1986-12-03
DE3641320		1986-12-03

Publications (2)

Publication Number	Publication Date
AU8196287A AU8196287A (en)	1988-06-16
AU605522B2 true AU605522B2 (en)	1991-01-17

Family

ID=6315380

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
AU81962/87A Ceased AU605522B2 (en)	1986-12-03	1987-12-01	Carboxamido ethyl-imidazole and-1,2,4-triazole derivatives

Country Status (24)

Country	Link
JP (1)	JPH0678318B2 (es)
KR (1)	KR880007481A (es)
AT (1)	AT395587B (es)
AU (1)	AU605522B2 (es)
BE (1)	BE1001235A4 (es)
CH (1)	CH677925A5 (es)
DK (1)	DK631287A (es)
ES (1)	ES2010235A6 (es)
FI (1)	FI875300L (es)
FR (1)	FR2607810B1 (es)
GB (1)	GB2199579B (es)
GR (1)	GR871897B (es)
HU (1)	HU198694B (es)
IL (1)	IL84665A (es)
IT (1)	IT1211944B (es)
LU (1)	LU87063A1 (es)
MY (1)	MY103004A (es)
NL (1)	NL8702897A (es)
NZ (1)	NZ222765A (es)
PH (1)	PH24666A (es)
PL (1)	PL151588B1 (es)
PT (1)	PT86255B (es)
SE (1)	SE8704792L (es)
ZA (1)	ZA879093B (es)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB8814277D0 (en) *	1988-06-16	1988-07-20	Glaxo Group Ltd	Chemical compounds
ATE186052T1 (de) *	1991-09-02	1999-11-15	Yamanouchi Pharma Co Ltd	Triazolylierte tertiäre aminverbindungen oder ihre salze
GB9409882D0 (en) *	1994-05-18	1994-07-06	Sandoz Ltd	Organic compounds
GB0128415D0 (en) *	2001-11-27	2002-01-16	Univ Sheffield	Medicaments

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AT382868B (de) *	1983-03-11	1987-04-27	Sandoz Ag	Verfahren zur herstellung neuer azolderivate und deren salze
JPH0625144B2 (ja) *	1986-02-24	1994-04-06	四国化成工業株式会社	新規イミダゾール化合物及び該化合物の合成方法

1987
- 1987-11-26 CH CH4607/87A patent/CH677925A5/de not_active IP Right Cessation
- 1987-11-30 GB GB8727978A patent/GB2199579B/en not_active Expired - Lifetime
- 1987-12-01 PH PH36145A patent/PH24666A/en unknown
- 1987-12-01 IL IL84665A patent/IL84665A/xx unknown
- 1987-12-01 MY MYPI87003136A patent/MY103004A/en unknown
- 1987-12-01 DK DK631287A patent/DK631287A/da not_active Application Discontinuation
- 1987-12-01 NZ NZ222765A patent/NZ222765A/en unknown
- 1987-12-01 FI FI875300A patent/FI875300L/fi not_active IP Right Cessation
- 1987-12-01 SE SE8704792A patent/SE8704792L/xx not_active Application Discontinuation
- 1987-12-01 AU AU81962/87A patent/AU605522B2/en not_active Ceased
- 1987-12-01 IT IT8748656A patent/IT1211944B/it active
- 1987-12-02 FR FR878716736A patent/FR2607810B1/fr not_active Expired
- 1987-12-02 BE BE8701375A patent/BE1001235A4/fr not_active IP Right Cessation
- 1987-12-02 HU HU875414A patent/HU198694B/hu unknown
- 1987-12-02 KR KR870013695A patent/KR880007481A/ko not_active Application Discontinuation
- 1987-12-02 JP JP62305522A patent/JPH0678318B2/ja not_active Expired - Lifetime
- 1987-12-02 AT AT0316887A patent/AT395587B/de not_active IP Right Cessation
- 1987-12-02 PL PL1987269180A patent/PL151588B1/pl unknown
- 1987-12-02 NL NL8702897A patent/NL8702897A/nl not_active Application Discontinuation
- 1987-12-02 PT PT86255A patent/PT86255B/pt not_active IP Right Cessation
- 1987-12-03 ZA ZA879093A patent/ZA879093B/xx unknown
- 1987-12-03 ES ES8703470A patent/ES2010235A6/es not_active Expired
- 1987-12-03 LU LU87063A patent/LU87063A1/fr unknown
- 1987-12-14 GR GR871897A patent/GR871897B/el unknown

Also Published As

Publication number	Publication date
IL84665A (en)	1991-11-21
LU87063A1 (fr)	1988-07-14
AT395587B (de)	1993-01-25
JPH0678318B2 (ja)	1994-10-05
FI875300A0 (fi)	1987-12-01
AU8196287A (en)	1988-06-16
PH24666A (en)	1990-09-07
FI875300L (fi)	1988-06-04
GB2199579A (en)	1988-07-13
MY103004A (en)	1993-03-31
DK631287A (da)	1988-06-04
IT1211944B (it)	1989-11-08
IT8748656A0 (it)	1987-12-01
CH677925A5 (es)	1991-07-15
PT86255A (en)	1988-06-01
SE8704792L (sv)	1988-06-04
NZ222765A (en)	1990-11-27
PL151588B1 (en)	1990-09-28
NL8702897A (nl)	1988-07-01
KR880007481A (ko)	1988-08-27
HU198694B (en)	1989-11-28
IL84665A0 (en)	1988-05-31
GB2199579B (en)	1990-07-18
JPS63145270A (ja)	1988-06-17
PL269180A1 (en)	1988-08-18
PT86255B (pt)	1990-11-07
ATA316887A (de)	1992-06-15
ZA879093B (en)	1989-07-26
DK631287D0 (da)	1987-12-01
SE8704792D0 (sv)	1987-12-01
HUT45506A (en)	1988-07-28
ES2010235A6 (es)	1989-11-01
FR2607810A1 (fr)	1988-06-10
BE1001235A4 (fr)	1989-08-29
GR871897B (en)	1988-04-04
GB8727978D0 (en)	1988-01-06
FR2607810B1 (fr)	1989-12-01

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AU605522B2 (en)	1991-01-17	Carboxamido ethyl-imidazole and-1,2,4-triazole derivatives
PT99738B (pt)	1999-05-31	Processo para a preparacao de compostos de fluor contendo por exemplo um grupo triazolilo
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JPS6112668A (ja)	1986-01-21	ピラゾール化合物
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US7098199B2 (en)	2006-08-29	Steroid sulphatase inhibitors
KR19990034285A (ko)	1999-05-15	항암활성을 갖는 육두구 추출물
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US4767770A (en)	1988-08-30	Method of inhibiting aromatase
US20160200685A1 (en)	2016-07-14	Substituted 1,2,3,4-tetrahydroisoquinoline derivatives for the treatment of hormone-dependent diseases
US4636496A (en)	1987-01-13	Compositions inhibiting murine MXT ductal carcinoma
GB2248058A (en)	1992-03-25	Aromatase inhibiting 4(5)-imidazoles
US20070021624A1 (en)	2007-01-25	Steroid sulphatase inhibitors
KR20000031736A (ko)	2000-06-05	항암활성을 갖는 초두구 추출물
DE3740125A1 (de)	1988-06-16	Azolderivate