CH677925A5 - - Google Patents

Download PDF

Info

Publication number: CH677925A5
Authority: CH; Switzerland
Prior art keywords: compounds; formula; acid addition; addition salts; phenyl
Prior art date: 1986-12-03

Application number

CH4607/87A

Other languages

German (de)

English (en)

Inventor

Helmut Dr Egger

Rudolf Dr Waelchli

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

1987-11-26

Publication date

1991-07-15

1987-11-26 Application filed by Sandoz Ag filed Critical Sandoz Ag

1991-07-15 Publication of CH677925A5 publication Critical patent/CH677925A5/de

Links

150000001875 compounds Chemical class 0.000 claims abstract description 48
239000002253 acid Substances 0.000 claims abstract description 19
150000003839 salts Chemical group 0.000 claims abstract description 19
125000003545 alkoxy group Chemical group 0.000 claims abstract description 14
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 13
125000003118 aryl group Chemical group 0.000 claims abstract description 10
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 10
239000003814 drug Substances 0.000 claims abstract description 9
125000001072 heteroaryl group Chemical group 0.000 claims abstract description 7
239000003886 aromatase inhibitor Substances 0.000 claims abstract description 4
229940046844 aromatase inhibitors Drugs 0.000 claims abstract description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 4
-1 mono-substituted phenyl Chemical group 0.000 claims description 17
102000014654 Aromatase Human genes 0.000 claims description 13
108010078554 Aromatase Proteins 0.000 claims description 13
125000004432 carbon atom Chemical group C* 0.000 claims description 11
238000000034 method Methods 0.000 claims description 8
125000000217 alkyl group Chemical group 0.000 claims description 7
238000004519 manufacturing process Methods 0.000 claims description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
125000005842 heteroatom Chemical group 0.000 claims description 5
230000002401 inhibitory effect Effects 0.000 claims description 4
239000000825 pharmaceutical preparation Substances 0.000 claims description 4
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 3
125000005418 aryl aryl group Chemical group 0.000 claims description 3
125000005605 benzo group Chemical group 0.000 claims description 3
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 3
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
229940079593 drug Drugs 0.000 claims description 3
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 description 3
229910052757 nitrogen Inorganic materials 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
125000006413 ring segment Chemical group 0.000 claims description 3
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims 2
125000004434 sulfur atom Chemical group 0.000 claims 2
125000000547 substituted alkyl group Chemical group 0.000 abstract 1
125000003107 substituted aryl group Chemical group 0.000 abstract 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 11
238000012360 testing method Methods 0.000 description 10
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
239000000126 substance Substances 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
210000001672 ovary Anatomy 0.000 description 6
241000700159 Rattus Species 0.000 description 5
230000005764 inhibitory process Effects 0.000 description 5
239000000047 product Substances 0.000 description 5
JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 5
125000001424 substituent group Chemical group 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
206010028980 Neoplasm Diseases 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
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
239000008280 blood Substances 0.000 description 4
210000004369 blood Anatomy 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
150000003431 steroids Chemical class 0.000 description 4
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 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-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
ROBVIMPUHSLWNV-UHFFFAOYSA-N aminoglutethimide Chemical compound C=1C=C(N)C=CC=1C1(CC)CCC(=O)NC1=O ROBVIMPUHSLWNV-UHFFFAOYSA-N 0.000 description 3
229960003437 aminoglutethimide Drugs 0.000 description 3
239000008346 aqueous phase Substances 0.000 description 3
238000001816 cooling Methods 0.000 description 3
230000000694 effects Effects 0.000 description 3
229940011871 estrogen Drugs 0.000 description 3
239000000262 estrogen Substances 0.000 description 3
125000005843 halogen group Chemical group 0.000 description 3
210000001589 microsome Anatomy 0.000 description 3
239000000203 mixture Substances 0.000 description 3
230000016087 ovulation Effects 0.000 description 3
239000003208 petroleum Substances 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
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 2
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
ARSRBNBHOADGJU-UHFFFAOYSA-N 7,12-dimethyltetraphene Chemical compound C1=CC2=CC=CC=C2C2=C1C(C)=C(C=CC=C1)C1=C2C ARSRBNBHOADGJU-UHFFFAOYSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
102000004190 Enzymes Human genes 0.000 description 2
108090000790 Enzymes Proteins 0.000 description 2
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
241000124008 Mammalia 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
230000010933 acylation Effects 0.000 description 2
238000005917 acylation reaction Methods 0.000 description 2
125000003342 alkenyl group Chemical group 0.000 description 2
125000000304 alkynyl group Chemical group 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
239000000969 carrier Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
230000001419 dependent effect Effects 0.000 description 2
229910052731 fluorine Inorganic materials 0.000 description 2
229910052736 halogen Inorganic materials 0.000 description 2
238000001727 in vivo Methods 0.000 description 2
239000003112 inhibitor Substances 0.000 description 2
239000011777 magnesium Substances 0.000 description 2
229910052749 magnesium Inorganic materials 0.000 description 2
229910052943 magnesium sulfate Inorganic materials 0.000 description 2
235000019341 magnesium sulphate Nutrition 0.000 description 2
210000000056 organ Anatomy 0.000 description 2
210000002826 placenta Anatomy 0.000 description 2
150000003254 radicals Chemical class 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
238000006467 substitution reaction Methods 0.000 description 2
229960003604 testosterone Drugs 0.000 description 2
UNQHORKHHWAMIR-UHFFFAOYSA-N 1,1-bis(4-chlorophenyl)-2-imidazol-1-ylethanamine Chemical compound ClC1=CC=C(C=C1)C(CN1C=NC=C1)(N)C1=CC=C(C=C1)Cl UNQHORKHHWAMIR-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
AYRABHFHMLXKBT-UHFFFAOYSA-N 2,6-Dimethyl-anthracen Natural products C1=C(C)C=CC2=CC3=CC(C)=CC=C3C=C21 AYRABHFHMLXKBT-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
208000026310 Breast neoplasm Diseases 0.000 description 1
VFZRZRDOXPRTSC-UHFFFAOYSA-N DMBA Natural products COC1=CC(OC)=CC(C=O)=C1 VFZRZRDOXPRTSC-UHFFFAOYSA-N 0.000 description 1
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
241001326189 Gyrodactylus prostae Species 0.000 description 1
101710162501 Ovarian aromatase Proteins 0.000 description 1
206010033128 Ovarian cancer Diseases 0.000 description 1
208000010067 Pituitary ACTH Hypersecretion Diseases 0.000 description 1
208000020627 Pituitary-dependent Cushing syndrome Diseases 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
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-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
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
239000007983 Tris buffer Substances 0.000 description 1
206010046782 Uterine enlargement Diseases 0.000 description 1
XJLXINKUBYWONI-DQQFMEOOSA-N [[(2r,3r,4r,5r)-5-(6-aminopurin-9-yl)-3-hydroxy-4-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2s,3r,4s,5s)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphate Chemical compound NC(=O)C1=CC=C[N+]([C@@H]2[C@H]([C@@H](O)[C@H](COP([O-])(=O)OP(O)(=O)OC[C@@H]3[C@H]([C@@H](OP(O)(O)=O)[C@@H](O3)N3C4=NC=NC(N)=C4N=C3)O)O2)O)=C1 XJLXINKUBYWONI-DQQFMEOOSA-N 0.000 description 1
210000004100 adrenal gland Anatomy 0.000 description 1
125000005431 alkyl carboxamide group Chemical group 0.000 description 1
125000004644 alkyl sulfinyl group Chemical group 0.000 description 1
125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
125000004414 alkyl thio group Chemical group 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
238000005899 aromatization reaction Methods 0.000 description 1
150000005840 aryl radicals Chemical class 0.000 description 1
150000007980 azole derivatives Chemical class 0.000 description 1
230000000903 blocking effect Effects 0.000 description 1
230000037396 body weight Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
201000008275 breast carcinoma Diseases 0.000 description 1
239000000872 buffer Substances 0.000 description 1
239000002775 capsule Substances 0.000 description 1
210000004027 cell Anatomy 0.000 description 1
210000003855 cell nucleus Anatomy 0.000 description 1
239000007795 chemical reaction product 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
125000004093 cyano group Chemical group *C#N 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
235000013601 eggs Nutrition 0.000 description 1
201000003914 endometrial carcinoma Diseases 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
238000002474 experimental method Methods 0.000 description 1
OSVMTWJCGUFAOD-KZQROQTASA-N formestane Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1O OSVMTWJCGUFAOD-KZQROQTASA-N 0.000 description 1
239000012458 free base Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
150000002367 halogens 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
238000000338 in vitro Methods 0.000 description 1
238000011534 incubation Methods 0.000 description 1
231100000546 inhibition of ovulation Toxicity 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
230000003228 microsomal effect Effects 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
229930027945 nicotinamide-adenine dinucleotide Natural products 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000008188 pellet Substances 0.000 description 1
230000003285 pharmacodynamic effect Effects 0.000 description 1
239000012071 phase Substances 0.000 description 1
238000005191 phase separation Methods 0.000 description 1
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
201000010065 polycystic ovary syndrome Diseases 0.000 description 1
210000002307 prostate Anatomy 0.000 description 1
239000002516 radical scavenger Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
239000013558 reference substance Substances 0.000 description 1
238000010992 reflux 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
239000000758 substrate Substances 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur 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
239000012730 sustained-release form Substances 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
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
210000004291 uterus Anatomy 0.000 description 1
238000011121 vaginal smear Methods 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

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Public Health (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Veterinary Medicine (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (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)

CH4607/87A 1986-12-03 1987-11-26 CH677925A5 (it)

Applications Claiming Priority (1)

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

Publications (1)

Publication Number	Publication Date
CH677925A5 true CH677925A5 (it)	1991-07-15

Family

ID=6315380

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH4607/87A CH677925A5 (it)	1986-12-03	1987-11-26

Country Status (24)

Country	Link
JP (1)	JPH0678318B2 (it)
KR (1)	KR880007481A (it)
AT (1)	AT395587B (it)
AU (1)	AU605522B2 (it)
BE (1)	BE1001235A4 (it)
CH (1)	CH677925A5 (it)
DK (1)	DK631287A (it)
ES (1)	ES2010235A6 (it)
FI (1)	FI875300A (it)
FR (1)	FR2607810B1 (it)
GB (1)	GB2199579B (it)
GR (1)	GR871897B (it)
HU (1)	HU198694B (it)
IL (1)	IL84665A (it)
IT (1)	IT1211944B (it)
LU (1)	LU87063A1 (it)
MY (1)	MY103004A (it)
NL (1)	NL8702897A (it)
NZ (1)	NZ222765A (it)
PH (1)	PH24666A (it)
PL (1)	PL151588B1 (it)
PT (1)	PT86255B (it)
SE (1)	SE8704792L (it)
ZA (1)	ZA879093B (it)

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
AU665569B2 (en) *	1991-09-02	1996-01-11	Yamanouchi Pharmaceutical Co., Ltd.	Triazolylated tertiary amine compound or salt thereof
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 NZ NZ222765A patent/NZ222765A/en unknown
- 1987-12-01 IL IL84665A patent/IL84665A/xx unknown
- 1987-12-01 AU AU81962/87A patent/AU605522B2/en not_active Ceased
- 1987-12-01 DK DK631287A patent/DK631287A/da not_active Application Discontinuation
- 1987-12-01 FI FI875300A patent/FI875300A/fi not_active IP Right Cessation
- 1987-12-01 IT IT8748656A patent/IT1211944B/it active
- 1987-12-01 MY MYPI87003136A patent/MY103004A/en unknown
- 1987-12-01 SE SE8704792A patent/SE8704792L/xx not_active Application Discontinuation
- 1987-12-01 PH PH36145A patent/PH24666A/en unknown
- 1987-12-02 PL PL1987269180A patent/PL151588B1/pl unknown
- 1987-12-02 PT PT86255A patent/PT86255B/pt not_active IP Right Cessation
- 1987-12-02 FR FR878716736A patent/FR2607810B1/fr not_active Expired
- 1987-12-02 KR KR870013695A patent/KR880007481A/ko not_active Application Discontinuation
- 1987-12-02 BE BE8701375A patent/BE1001235A4/fr not_active IP Right Cessation
- 1987-12-02 JP JP62305522A patent/JPH0678318B2/ja not_active Expired - Lifetime
- 1987-12-02 NL NL8702897A patent/NL8702897A/nl not_active Application Discontinuation
- 1987-12-02 HU HU875414A patent/HU198694B/hu unknown
- 1987-12-02 AT AT0316887A patent/AT395587B/de not_active IP Right Cessation
- 1987-12-03 LU LU87063A patent/LU87063A1/fr unknown
- 1987-12-03 ZA ZA879093A patent/ZA879093B/xx unknown
- 1987-12-03 ES ES8703470A patent/ES2010235A6/es not_active Expired
- 1987-12-14 GR GR871897A patent/GR871897B/el unknown

Also Published As

Publication number	Publication date
GB2199579B (en)	1990-07-18
AU605522B2 (en)	1991-01-17
NZ222765A (en)	1990-11-27
IL84665A (en)	1991-11-21
ES2010235A6 (es)	1989-11-01
LU87063A1 (fr)	1988-07-14
SE8704792L (sv)	1988-06-04
IT8748656A0 (it)	1987-12-01
HUT45506A (en)	1988-07-28
AT395587B (de)	1993-01-25
DK631287D0 (da)	1987-12-01
PT86255A (en)	1988-06-01
ATA316887A (de)	1992-06-15
BE1001235A4 (fr)	1989-08-29
FR2607810B1 (fr)	1989-12-01
PT86255B (pt)	1990-11-07
JPS63145270A (ja)	1988-06-17
FR2607810A1 (fr)	1988-06-10
PL269180A1 (en)	1988-08-18
GB2199579A (en)	1988-07-13
SE8704792D0 (sv)	1987-12-01
NL8702897A (nl)	1988-07-01
IL84665A0 (en)	1988-05-31
GB8727978D0 (en)	1988-01-06
ZA879093B (en)	1989-07-26
FI875300A (fi)	1988-06-04
GR871897B (en)	1988-04-04
IT1211944B (it)	1989-11-08
MY103004A (en)	1993-03-31
PL151588B1 (en)	1990-09-28
AU8196287A (en)	1988-06-16
JPH0678318B2 (ja)	1994-10-05
DK631287A (da)	1988-06-04
PH24666A (en)	1990-09-07
HU198694B (en)	1989-11-28
KR880007481A (ko)	1988-08-27
FI875300A0 (fi)	1987-12-01

Publication	Publication Date	Title
DE3218584C2 (it)	1989-11-02
EP0770613A1 (de)	1997-05-02	Substituierte Imidazolidin-2,4-dion-Verbindungen als Immunodulatore
US4304782A (en)	1981-12-08	Psychotropic deuterated derivatives of phenylhydantoin and pharmaceutical compositions comprising such derivatives
DE69828999T2 (de)	2005-07-21	1-(4-(1-(4-fluorophenyl)-1h-indol-3-yl)1-butyl)-spiro-(isobenzofuran-1(3h),4'-pperidin)-hydrohalogenide
DE2455353C3 (de)	1979-08-09	Substituierte a -Aminooxvcarbonsäurehydrazidderivate und ihre Säureadditionssalze sowie ihre Verwendung vnd Verfahren zur Herstellung derselben
EP0304534A1 (de)	1989-03-01	Dihydropyridazinon-Derivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
DE2737738C2 (de)	1987-01-29	3-Amino-thiophen-4-carbonsäuren und deren Derivate, Verfahren zu deren Herstellung und diese enthaltende pharmazeutische Mittel
AT395587B (de)	1993-01-25	Herstellung und verwendung neuer azolderivate, und sie enthaltende pharmazeutische praeparate
EP0411735A1 (de)	1991-02-06	Cycloakylenazole, Verfahren zu deren Herstellung, pharmazeutische Präparate, die diese enthalten sowie ihre Verwendung zur Herstellung von Arzneimitteln
DE3877124T2 (de)	1993-04-29	Imidazol-derivate, verfahren zu deren herstellung und deren anwendung als alpha-2-adrenoceptor-antagonisten.
DE1470284B1 (de)	1971-12-16	Beta-{1-Methyl-4-[1-methyl-4-(1-methyl-4-formylamino-pyrrol-2-carboxamido)-pyrrol-2-carboxamido]-pyrrol-2-carboxamido}-propionamidin sowie dessen Saeureadditionssalze
EP0283857A1 (de)	1988-09-28	Benzylidenamino-, benzylamino- und benzoylamino-imidazolderivate
DE3740125A1 (de)	1988-06-16	Azolderivate
EP0003286B1 (de)	1982-03-24	Ergopeptidalkaloid-Derivate, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Zusammensetzungen
DE2917890C2 (it)	1987-10-29
DE2148552A1 (de)	1972-04-06	Verfahren zur Herstellung neuer heterocyclischer Verbindungen
DE3129719C2 (de)	1984-04-26	Pharmazeutisches Mittel
DE2614137C2 (de)	1983-02-03	Benzo[b]thien(2)-ylaminoäthylketone, Verfahren zu ihrer Herstellung, sowie diese enthaltende Arzneimittel
DE69018741T2 (de)	1995-10-12	Konjugierte gamma-Hydroxybutenolid-Derivate und sie als aktiver Wirkstoff enthaltende Mittel gegen Magengeschwüre.
DE1468681C3 (de)	1973-09-27	17beta-Tetrahydropyranyloxy verbindungen der Androstanreihe sowie Verfahren zu ihrer Herstellung und Heilmittel
EP0004261B1 (de)	1982-04-28	Neue Imidazolderivate, Verfahren zu deren Herstellung und Arzneimittel diese enthaltend
DE1470284C (de)	1972-07-20	beta- geschweifte Klammer auf 1-Methyl-4- eckige Klammer auf l-methyl-4-(l-methyl-4-fonnylamino-pyrrol-2-carboxamido)-pyrrol-2-carboxamido eckige Klammer zu -pyrrol-2carboxamido geschweifte Klammer zu -propionamidin sowie dessen Säureadditionssalze
CH615181A5 (en)	1980-01-15	Process for the preparation of novel ergolene derivatives
DE2031238C3 (de)	1977-02-17	i.a-Diphenyl-S.S-dioxo^-substituierter Pyrazolidine, Verfahren zu deren Herstellung und Arzneimittel
AT389310B (de)	1989-11-27	Cyclohexandion-derivat und verfahren zu seiner herstellung

Legal Events

Date	Code	Title	Description
1994-07-29	PL	Patent ceased
2024-10-31	PL	Patent ceased