SI9420058B - Biciklične aromatske spojine kot terapevtska sredstva - Google Patents
Biciklične aromatske spojine kot terapevtska sredstva Download PDFInfo
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- SI9420058B SI9420058B SI9420058A SI9420058A SI9420058B SI 9420058 B SI9420058 B SI 9420058B SI 9420058 A SI9420058 A SI 9420058A SI 9420058 A SI9420058 A SI 9420058A SI 9420058 B SI9420058 B SI 9420058B
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- benzodioxan
- ylmethyl
- methylamine
- piperid
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- -1 Bicyclic aromatic compounds Chemical class 0.000 title claims 6
- 239000003814 drug Substances 0.000 title claims 3
- 229940124597 therapeutic agent Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 26
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims abstract 8
- 150000003839 salts Chemical class 0.000 claims abstract 4
- 125000002947 alkylene group Chemical group 0.000 claims abstract 3
- 208000028017 Psychotic disease Diseases 0.000 claims abstract 2
- 125000000217 alkyl group Chemical group 0.000 claims abstract 2
- 201000000980 schizophrenia Diseases 0.000 claims abstract 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 6
- 125000004432 carbon atom Chemical group C* 0.000 claims 5
- 125000005843 halogen group Chemical group 0.000 claims 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 2
- 150000002466 imines Chemical class 0.000 claims 2
- OLSUMCUJAFRBLY-UHFFFAOYSA-N n-(2,3-dihydro-1,4-benzodioxin-3-ylmethyl)-1-(1-pyridin-2-ylpiperidin-4-yl)methanamine;dihydrochloride Chemical compound Cl.Cl.C1OC2=CC=CC=C2OC1CNCC(CC1)CCN1C1=CC=CC=N1 OLSUMCUJAFRBLY-UHFFFAOYSA-N 0.000 claims 2
- QHLRKDSRGUZHSH-UHFFFAOYSA-N n-[(6-chloro-2,3-dihydro-1,4-benzodioxin-3-yl)methyl]-1-[1-(2-methoxyphenyl)piperidin-4-yl]methanamine Chemical compound COC1=CC=CC=C1N1CCC(CNCC2OC3=CC(Cl)=CC=C3OC2)CC1 QHLRKDSRGUZHSH-UHFFFAOYSA-N 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- CSWPZFOPVQMWKT-UHFFFAOYSA-N 1-[1-(2-chlorophenyl)piperidin-4-yl]-n-(2,3-dihydro-1,4-benzodioxin-3-ylmethyl)methanamine Chemical compound ClC1=CC=CC=C1N1CCC(CNCC2OC3=CC=CC=C3OC2)CC1 CSWPZFOPVQMWKT-UHFFFAOYSA-N 0.000 claims 1
- XAQVIYHHHMUNRP-UHFFFAOYSA-N 1-[1-(3-chloropyridin-2-yl)piperidin-4-yl]-n-(2,3-dihydro-1,4-benzodioxin-3-ylmethyl)methanamine Chemical compound ClC1=CC=CN=C1N1CCC(CNCC2OC3=CC=CC=C3OC2)CC1 XAQVIYHHHMUNRP-UHFFFAOYSA-N 0.000 claims 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 1
- 239000005977 Ethylene Chemical group 0.000 claims 1
- GLNSZRIRDSNHGH-UHFFFAOYSA-N [1-(2,3-dihydro-1,4-benzodioxin-3-ylmethyl)piperidin-4-yl]-(2-methoxyphenyl)methanamine Chemical compound COC1=CC=CC=C1C(N)C1CCN(CC2OC3=CC=CC=C3OC2)CC1 GLNSZRIRDSNHGH-UHFFFAOYSA-N 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 239000003638 chemical reducing agent Substances 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- DXFCGSGBNDZTRJ-UHFFFAOYSA-N n-(2,3-dihydro-1,4-benzodioxin-3-ylmethyl)-1-(1-phenylpiperidin-4-yl)methanamine Chemical compound C1OC2=CC=CC=C2OC1CNCC(CC1)CCN1C1=CC=CC=C1 DXFCGSGBNDZTRJ-UHFFFAOYSA-N 0.000 claims 1
- QYIVXYLXNBZISL-UHFFFAOYSA-N n-(2,3-dihydro-1,4-benzodioxin-3-ylmethyl)-1-(1-pyrazin-2-ylpiperidin-4-yl)methanamine Chemical compound C1OC2=CC=CC=C2OC1CNCC(CC1)CCN1C1=CN=CC=N1 QYIVXYLXNBZISL-UHFFFAOYSA-N 0.000 claims 1
- LTWGNOKBPCXOOT-UHFFFAOYSA-N n-(2,3-dihydro-1,4-benzodioxin-3-ylmethyl)-1-(1-pyridin-2-ylpiperidin-4-yl)methanamine Chemical compound C1OC2=CC=CC=C2OC1CNCC(CC1)CCN1C1=CC=CC=N1 LTWGNOKBPCXOOT-UHFFFAOYSA-N 0.000 claims 1
- DIPCVHNBWIDIIZ-UHFFFAOYSA-N n-(2,3-dihydro-1,4-benzodioxin-3-ylmethyl)-1-(1-quinazolin-4-ylpiperidin-4-yl)methanamine Chemical compound C1=CC=C2C(N3CCC(CC3)CNCC3OC4=CC=CC=C4OC3)=NC=NC2=C1 DIPCVHNBWIDIIZ-UHFFFAOYSA-N 0.000 claims 1
- OGFDOBGWVXITBG-UHFFFAOYSA-N n-(2,3-dihydro-1,4-benzodioxin-3-ylmethyl)-1-[1-(2,3-dihydro-1,4-benzodioxin-5-yl)piperidin-4-yl]methanamine Chemical compound O1CCOC2=C1C=CC=C2N(CC1)CCC1CNCC1OC2=CC=CC=C2OC1 OGFDOBGWVXITBG-UHFFFAOYSA-N 0.000 claims 1
- XYBADQIMVGSILK-UHFFFAOYSA-N n-(2,3-dihydro-1,4-benzodioxin-3-ylmethyl)-1-[1-(2-methoxyphenyl)piperidin-4-yl]methanamine Chemical compound COC1=CC=CC=C1N1CCC(CNCC2OC3=CC=CC=C3OC2)CC1 XYBADQIMVGSILK-UHFFFAOYSA-N 0.000 claims 1
- DUTPDVWPQWRHMS-UHFFFAOYSA-N n-(2,3-dihydro-1,4-benzodioxin-3-ylmethyl)-1-[1-(3-methoxyphenyl)piperidin-4-yl]methanamine Chemical compound COC1=CC=CC(N2CCC(CNCC3OC4=CC=CC=C4OC3)CC2)=C1 DUTPDVWPQWRHMS-UHFFFAOYSA-N 0.000 claims 1
- CAUVIHGEFYOEKK-UHFFFAOYSA-N n-(2,3-dihydro-1,4-benzodioxin-3-ylmethyl)-1-[1-(4-methoxyphenyl)piperidin-4-yl]methanamine Chemical compound C1=CC(OC)=CC=C1N1CCC(CNCC2OC3=CC=CC=C3OC2)CC1 CAUVIHGEFYOEKK-UHFFFAOYSA-N 0.000 claims 1
- LCBNYESLHUNVRV-UHFFFAOYSA-N n-[(5-fluoro-2,3-dihydro-1,4-benzodioxin-2-yl)methyl]-1-[1-(2-methoxyphenyl)piperidin-4-yl]methanamine Chemical compound COC1=CC=CC=C1N1CCC(CNCC2OC3=CC=CC(F)=C3OC2)CC1 LCBNYESLHUNVRV-UHFFFAOYSA-N 0.000 claims 1
- MVTOIWYCUADBKD-UHFFFAOYSA-N n-[(5-fluoro-2,3-dihydro-1,4-benzodioxin-3-yl)methyl]-1-[1-(2-methoxyphenyl)piperidin-4-yl]methanamine Chemical compound COC1=CC=CC=C1N1CCC(CNCC2OC3=C(F)C=CC=C3OC2)CC1 MVTOIWYCUADBKD-UHFFFAOYSA-N 0.000 claims 1
- VOHRNHMSMCXPTR-UHFFFAOYSA-N n-[(5-methoxy-2,3-dihydro-1,4-benzodioxin-3-yl)methyl]-1-[1-(2-methoxyphenyl)piperidin-4-yl]methanamine Chemical compound COC1=CC=CC=C1N1CCC(CNCC2OC3=C(OC)C=CC=C3OC2)CC1 VOHRNHMSMCXPTR-UHFFFAOYSA-N 0.000 claims 1
- VECANYISKSOUJK-UHFFFAOYSA-N n-[(6-chloro-2,3-dihydro-1,4-benzodioxin-2-yl)methyl]-1-[1-(2-methoxyphenyl)piperidin-4-yl]methanamine Chemical compound COC1=CC=CC=C1N1CCC(CNCC2OC3=CC=C(Cl)C=C3OC2)CC1 VECANYISKSOUJK-UHFFFAOYSA-N 0.000 claims 1
- XYBADQIMVGSILK-GOSISDBHSA-N n-[[(3r)-2,3-dihydro-1,4-benzodioxin-3-yl]methyl]-1-[1-(2-methoxyphenyl)piperidin-4-yl]methanamine Chemical compound COC1=CC=CC=C1N1CCC(CNC[C@H]2OC3=CC=CC=C3OC2)CC1 XYBADQIMVGSILK-GOSISDBHSA-N 0.000 claims 1
- XYBADQIMVGSILK-SFHVURJKSA-N n-[[(3s)-2,3-dihydro-1,4-benzodioxin-3-yl]methyl]-1-[1-(2-methoxyphenyl)piperidin-4-yl]methanamine Chemical compound COC1=CC=CC=C1N1CCC(CNC[C@@H]2OC3=CC=CC=C3OC2)CC1 XYBADQIMVGSILK-SFHVURJKSA-N 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims 1
- 125000003373 pyrazinyl group Chemical group 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 abstract 2
- 208000011117 substance-related disease Diseases 0.000 abstract 2
- 208000019901 Anxiety disease Diseases 0.000 abstract 1
- 206010004446 Benign prostatic hyperplasia Diseases 0.000 abstract 1
- 208000024172 Cardiovascular disease Diseases 0.000 abstract 1
- 206010010774 Constipation Diseases 0.000 abstract 1
- 206010013654 Drug abuse Diseases 0.000 abstract 1
- 208000030814 Eating disease Diseases 0.000 abstract 1
- 208000019454 Feeding and Eating disease Diseases 0.000 abstract 1
- 206010020772 Hypertension Diseases 0.000 abstract 1
- 208000008238 Muscle Spasticity Diseases 0.000 abstract 1
- 208000008589 Obesity Diseases 0.000 abstract 1
- 206010033664 Panic attack Diseases 0.000 abstract 1
- 208000018737 Parkinson disease Diseases 0.000 abstract 1
- 208000004403 Prostatic Hyperplasia Diseases 0.000 abstract 1
- 206010039966 Senile dementia Diseases 0.000 abstract 1
- 201000001880 Sexual dysfunction Diseases 0.000 abstract 1
- 206010043118 Tardive Dyskinesia Diseases 0.000 abstract 1
- 208000000323 Tourette Syndrome Diseases 0.000 abstract 1
- 208000016620 Tourette disease Diseases 0.000 abstract 1
- 208000022531 anorexia Diseases 0.000 abstract 1
- 230000036506 anxiety Effects 0.000 abstract 1
- 206010003119 arrhythmia Diseases 0.000 abstract 1
- 230000006793 arrhythmia Effects 0.000 abstract 1
- 208000015114 central nervous system disease Diseases 0.000 abstract 1
- 208000026106 cerebrovascular disease Diseases 0.000 abstract 1
- 208000010877 cognitive disease Diseases 0.000 abstract 1
- 206010061428 decreased appetite Diseases 0.000 abstract 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract 1
- 208000035475 disorder Diseases 0.000 abstract 1
- 235000014632 disordered eating Nutrition 0.000 abstract 1
- 206010013663 drug dependence Diseases 0.000 abstract 1
- 230000002526 effect on cardiovascular system Effects 0.000 abstract 1
- 201000001421 hyperglycemia Diseases 0.000 abstract 1
- 210000000607 neurosecretory system Anatomy 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 235000020824 obesity Nutrition 0.000 abstract 1
- 208000019906 panic disease Diseases 0.000 abstract 1
- 201000004240 prostatic hypertrophy Diseases 0.000 abstract 1
- 231100000872 sexual dysfunction Toxicity 0.000 abstract 1
- 208000018198 spasticity Diseases 0.000 abstract 1
- 208000001072 type 2 diabetes mellitus Diseases 0.000 abstract 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
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- 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
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- 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
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- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
- C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
- C07D319/16—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D319/20—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring with substituents attached to the hetero ring
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
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- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
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Claims (10)
1 Patentni zahtevki 1. Spojine s formulo I
in njihove farmacevtsko sprejemljive soli v obliki posameznih enantiomerov, racematov ali drugih zmesi enantiomerov, kjer je A -O-; B-0-; gOali 1; Rj predstavlja halo, alkilno skupino z 1 do 3 atomi ogljika, alkoksi skupino z 1 do 3 atomi ogljika ali hidroksi; R2, R3 in R4 so vsak H; Uje metilen; Q je skupina s formulo Ha ali Ilc Rj -N—V
\ IU X
ne
-N / \ X* kjer je V metilen ali etilen, X je alkilenska veriga z 0 do 2 atomoma ogljika in je X' alkilenska veriga z 1 do 4 atomi ogljika, pod pogojem, da celotno število ataomov ogljika v X in X' znaša 3 ali 4; in je R5 H; in je T piridil, pirazinil, fenil, benzo[b]furanil, 1-4-benzodioksanil ali kinazolinil, pri čemer so vsi v danem primeru substituirani z metoksi, trifluorometilom ali halo.
2. Spojine s formulo I po zahtevku 1, označene s tem, da K\ predstavlja metoksi, fluoro, kloro ali hidroksi. 2
3. Spojine s formulo I po zahtevku 1, označene s tem, da je T 2-piridil, 2-pirazinil, fenil, 2,3-dihidrobenzo(b)furan-7-il, l,4-benzodioksan-5-il ali 4-kinazolinil, pri čemer so vsi v danem primeru substituirani z metoksi, trifluorometilom ali halo.
4. Spojine s formulo I po zahtevku 1, označene s tem, da jih izberemo izmed naslednjih, kot so: N-(l,4-benzodioksan-2-ilmetil)l-[l-(pirazin-2-il)piperid-4-il]metilamin; N-( 1,4-benzodioksan-2-ilmetil) 1 -[ 1 -(2-metoksifenil)piperid-4-il]metilamin; N-(l,4-benzodioksan-2-ilmetil)l-[l-(3-kloropirid-2-il)piperid-4-il]metilamin; N-( 1,4-benzodioksan-2-ilmetil) 1 - [ 1 -(kinazolin-4-il)piperid-4-il]metilamin; N-( 1,4-benzodioksan-2-ilmetil)-1 -[ 1 -(pirid-2-il)piperid-4-il]metilamin; N-(8-metoksi-1,4-benzodioksan-2-ilmetil) 1 - [ 1 -(2-metoksifenil)piperid-4-il]metilamin; N-( 1,4-benzodioksan-2-ilmetil) 1 -(1 -fenilpiperid-4-il)metilamin; N-( 1,4-benzodioksan-2-ilmetil)-1 - [ 1 -(1,4-benzodioksan-5-il)piperid-4-il]metilamin; 1 - [ 1 -(1,4-benzodioksan-2-ilmetil)piperid-4-il]-N-(2-metoksifenil)metilamin; N-( 1,4-benzodioksan-2-ilmetil)-1 -[ 1 -(4-metoksifenil)piperid-4-il]metilamin; N-( 1,4-benzodioksan-2-ilmetil)-1 -[ 1 -(3-metoksifenil)piperid-4-il]metilamin; N-( 1,4-benzodioksan-2-ilmetil)-1 - [ 1 -(2-klorofenil)piperid-4-il]metilamin; N-(5-fluoro-1,4-benzodioksan-2-ilmetil)-1 -[ 1 -(2-metoksifenil)piperid-4-il]metilamin; N-(8-fluoro-1,4-benzodioksan-2-ilmetil)-1 -[ 1 -(2-metoksifenil)piperid-4-il]metilamin; N-1 -[1 -(2,3-dihidrobenzo[b]furan-7-il)piperid-4-il]-N-(8-metoksi-1,4-benzodioksan-2-ilmetil)metilamin; N-(6-kloro-1,4-benzodioksan-2-ilmetil) 1 -[ 1 -(2-metoksifenil)piperid-4-il]metilamin; N-(7-kloro-1,4-benzodioksan-2-ilmetil)-1 -[ 1 -(2-metoksifenil)piperid-4-il]metilamin; N-(8-hidroksi-1,4-benzodioksan-2-ilmetil)-1 -[ 1 -(2-metoksifenil)piperid-4-iljmetilamin; in njihove farmacevtsko sprejemljive soli v obliki posameznih enantiomerov, racematov ali drugih zmesi enantiomerov.
5. Spojine s formulo I po zahtevku 4, označene s tem, da so: (S)-(-)-N-(l,4-benzodioksan-2-ilmetil)-l-[l-(2-metoksifenil)piperid-4-il]metilamin; 3 (R)- (+)-N-( 1,4-benzodioksan-2-ilmetil)-1 -[ 1 -(2-metoksifenil)piperid-4-il]metilamin; (-)-N-( 1,4-benzodioksan-2-ilmetil)-1 - [ 1 -(pirid-2-il)piperid-4-il]metilamin dihidroklorid; (+)-N-( 1,4-benzodioksan-2-ilmetil)-1 -[ 1 -(pirid-2-il)piperid-4-il]metilamin dihidroklorid.
6. Spojina s formulo I po zahtevku 4, označena s tem, daje: N-(7-kloro-1,4-benzodioksan-2-ilmetil)-1 -(1 -(2-metoksifenil)piperid-4-il)metilamin; in njene farmacevtsko sprejemljive soli v obliki posameznih enantiomerov, racematov ali drugih zmesi enantiomerov.
7. Farmacevtski sestavek, označen s tem, da obsega terapevtsko učinkovito količino spojine s formulo I po zahtevku 1 skupaj s farmacevtsko sprejemljivim razredčilom ali nosilcem.
8. Spojina s formulo I po zahtevkih 1 do 6 za uporabo kot zdravilo za zdravljenje psihoz.
9. Spojina s formulo I po zahtevku 8 za uporabo kot zdravilo za zdravljenje shizofrenije.
10. Postopek za pripravo spojin s formulo I, kot so definirane v zahtevku 1, označen s tem, da obsega a) reakcijo spojine s formulo III
nr s spojino s formulo IV X o
N—T \/ IV 4 temu pa sledi reakcija intermediatnega imina z reducimim sredstvom, da dobimo spojine s formulo I, kjer je Q skupina s formulo Ha, kjer je R5 H in je V (CH2)n+i, kjer je n 0 ali 1; b) reakcijo spojine s formulo III s spojino s formulo V v / X\ Y—-CH,—(CHji,—< N-T X / X1 kjer je Y odhodna skupina, da dobimo spojine s formulo I, kjer je Q skupina s formulo Ha, kjer je R5 H in je V (CH2)n+i, kjer je n 0 ali 1; c) reakcijo spojine s formulo VI X HiN-CHj-iCHai.
\ N-T VI / s spojino s formulo VII X1
kjer je Z odhodna skupina, da dobimo spojine s formulo I, kjer je Q skupina s formulo Ha, kjer je R5 H in je V (CH2)n+1, kjer je n 0; d) reakcijo spojin s formulo VI s spojinami s formulo VIII
čemur sledi redukcija intermediatnega imina, da dobimo spojine s formulo I, kjer je U metilen, Q je skupina s formulo Ha, kjer je R5 H in je V (CH2)n+i, kjer je n 0 ali 1; ali e) reakcijo spojine s formulo XLII 5
s haloaromatsko spojino, da dobimo spojine s formulo I, kjer je Q skupina s formulo Ilc.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB939318431A GB9318431D0 (en) | 1993-09-06 | 1993-09-06 | Therapeutic agents |
| PCT/EP1994/002904 WO1995007274A1 (en) | 1993-09-06 | 1994-09-01 | Bicyclic aromatic compounds as therapeutic agents |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SI9420058A SI9420058A (en) | 1996-12-31 |
| SI9420058B true SI9420058B (sl) | 2002-02-28 |
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| Application Number | Title | Priority Date | Filing Date |
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| SI9420058A SI9420058B (sl) | 1993-09-06 | 1994-09-01 | Biciklične aromatske spojine kot terapevtska sredstva |
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| Country | Link |
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| US (1) | US5767116A (sl) |
| EP (1) | EP0717739B1 (sl) |
| JP (1) | JPH09502431A (sl) |
| KR (1) | KR100325964B1 (sl) |
| CN (1) | CN1052723C (sl) |
| AT (1) | ATE191214T1 (sl) |
| AU (1) | AU689802B2 (sl) |
| BG (1) | BG63272B1 (sl) |
| BR (1) | BR9407413A (sl) |
| CA (1) | CA2170056A1 (sl) |
| CZ (1) | CZ61496A3 (sl) |
| DE (1) | DE69423767T2 (sl) |
| DK (1) | DK0717739T3 (sl) |
| ES (1) | ES2144528T3 (sl) |
| FI (1) | FI961016A0 (sl) |
| GB (1) | GB9318431D0 (sl) |
| GR (1) | GR3033575T3 (sl) |
| HU (1) | HUT75875A (sl) |
| IL (1) | IL110844A (sl) |
| NO (1) | NO308536B1 (sl) |
| NZ (1) | NZ273581A (sl) |
| PL (1) | PL178270B1 (sl) |
| PT (1) | PT717739E (sl) |
| RO (1) | RO116811B1 (sl) |
| RU (1) | RU2136680C1 (sl) |
| SI (1) | SI9420058B (sl) |
| SK (1) | SK27196A3 (sl) |
| TW (1) | TW311137B (sl) |
| UA (1) | UA41952C2 (sl) |
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| ZA (1) | ZA946798B (sl) |
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| GB9514380D0 (en) * | 1995-07-13 | 1995-09-13 | Knoll Ag | Therapeutic agents |
| FR2738823B1 (fr) * | 1995-09-15 | 1997-10-31 | Synthelabo | Derives de 3-(omega-(4-(thieno(3,2-c)pyridin-4-yl)piperazin- 1-yl)alkyl)-3,4-dihydroquinolein-2(1h)-one,leur preparation et leur application en therapeutique |
| GB9526495D0 (en) * | 1995-12-23 | 1996-02-28 | Knoll Ag | Therapeutic agents |
| DE19624154A1 (de) | 1996-06-18 | 1998-01-08 | Hoechst Ag | Ringannelierte Dihydropyrane, Verfahren zur Herstellung sowie deren Verwendung |
| GB9627006D0 (en) * | 1996-12-27 | 1997-02-12 | Knoll Ag | Therapeutic agents |
| GB9627005D0 (en) * | 1996-12-27 | 1997-02-12 | Knoll Ag | Therapeutic agents |
| FR2760014B1 (fr) * | 1997-02-27 | 1999-04-09 | Adir | Nouveaux composes de 2-amino indane, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| GB9704948D0 (en) * | 1997-03-11 | 1997-04-30 | Knoll Ag | Therapeutic agents |
| FR2761358B1 (fr) * | 1997-03-27 | 1999-05-07 | Adir | Nouveaux composes de n-aryl piperidine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| US6034256A (en) | 1997-04-21 | 2000-03-07 | G.D. Searle & Co. | Substituted benzopyran derivatives for the treatment of inflammation |
| US6077850A (en) | 1997-04-21 | 2000-06-20 | G.D. Searle & Co. | Substituted benzopyran analogs for the treatment of inflammation |
| GB9811879D0 (en) * | 1998-06-03 | 1998-07-29 | Knoll Ag | Therapeutic agents |
| FR2780057B1 (fr) * | 1998-06-18 | 2002-09-13 | Sanofi Sa | Phenoxypropanolamines, procede pour leur preparation et compositions pharmaceutiques les contenant |
| FR2782515B1 (fr) * | 1998-08-21 | 2000-09-22 | Adir | NOUVEAUX DERIVES DE L'INDANE-1-Ol, LEUR PROCEDE DE PREPARATION ET LES COMPOSITIONS PHARMACEUTIQUES QUI LES CONTIENNENT |
| GB9915616D0 (en) * | 1999-07-05 | 1999-09-01 | Knoll Ag | Therapeutic agents |
| GB0007376D0 (en) * | 2000-03-28 | 2000-05-17 | Knoll Ag | Therapeutic agents |
| US6458804B1 (en) * | 2001-01-26 | 2002-10-01 | R.T. Alamo Venturesi, Llc | Methods for the treatment of central nervous system disorders in certain patient groups |
| US6656951B2 (en) | 2001-04-24 | 2003-12-02 | Wyeth | 8-aza-bicyclo[3.2.1]octan-3-ol derivatives of 2,3-dihydro-1,4-benzodioxan as 5-HT1A antagonists |
| US6656950B2 (en) | 2001-04-25 | 2003-12-02 | Wyeth | Antidepressant azaheterocyclylmethyl derivatives of 1,4-dioxino[2,3-b]pyridine |
| EP1381612A1 (en) * | 2001-04-26 | 2004-01-21 | Wyeth | Antidepressant aza-heterocyclylmethyl derivatives of 2,3-dihydro-1,4-dioxino[2,3-f]quinazoline |
| DE10120619A1 (de) * | 2001-04-26 | 2002-10-31 | Merck Patent Gmbh | 2-(5-(4-Fluorphenyl)-3-pyridylmethylaminomethyl-chroman |
| GB0112836D0 (en) | 2001-05-25 | 2001-07-18 | Smithkline Beecham Plc | Medicaments |
| US6667322B2 (en) | 2001-10-05 | 2003-12-23 | Wyeth | Antidepressant chroman and chromene derivatives of 3-(1,2,3,6-tetrahydro-4-pyridinyl)-1H-indole |
| US7153849B2 (en) * | 2002-09-12 | 2006-12-26 | Wyeth | Antidepressant arylpiperazine derivatives of hetrocycle-fused benzodioxans |
| US6939877B2 (en) * | 2002-09-12 | 2005-09-06 | Wyeth | Antidepressant piperidine derivatives of heterocycle-fused benzodioxans |
| US6911445B2 (en) * | 2002-09-12 | 2005-06-28 | Wyeth | Antidepressant cycloalkylamine derivatives of heterocycle-fused benzodioxans |
| US6800637B2 (en) * | 2002-09-12 | 2004-10-05 | Wyeth | Antidepressant indolealkyl derivatives of heterocycle-fused benzodioxan methylamines |
| FR2884251B1 (fr) * | 2005-04-08 | 2007-07-13 | Servier Lab | Derives de piperazine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| PL1888548T3 (pl) | 2005-05-26 | 2013-01-31 | Neuron Systems Inc | Pochodna chinoliny do leczenia schorzeń siatkówki |
| TWI457122B (zh) | 2007-07-20 | 2014-10-21 | Orion Corp | 作為用於治療周邊和中央神經系統疾病之alpha2C拮抗劑的2,3－二氫苯並[1,4]戴奧辛－2－基甲基衍生物 |
| CA2782015C (en) | 2009-12-11 | 2020-08-25 | Neuron Systems, Inc. | Topical ophthalmic compositions and methods for the treatment of macular degeneration |
| JP2019519582A (ja) | 2016-06-29 | 2019-07-11 | オリオン コーポレーション | ベンゾジオキサン誘導体およびその医薬用途 |
| US12006298B2 (en) | 2018-08-06 | 2024-06-11 | Aldeyra Therapeutics, Inc. | Polymorphic compounds and uses thereof |
| CA3137301A1 (en) | 2019-05-02 | 2020-11-05 | Aldeyra Therapeutics, Inc. | Polymorphic compounds and uses thereof |
| US12098132B2 (en) | 2019-05-02 | 2024-09-24 | Aldeyra Therapeutics, Inc. | Process for preparation of aldehyde scavenger and intermediates |
| EP4149470A4 (en) | 2020-05-13 | 2024-04-24 | Aldeyra Therapeutics, Inc. | PHARMACEUTICAL FORMULATIONS AND USES THEREOF |
| IL309524A (en) * | 2021-07-02 | 2024-02-01 | Aldeyra Therapeutics Inc | Heterocyclic aldehyde scavenging compounds and uses thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US4684739A (en) * | 1980-12-15 | 1987-08-04 | Mitsubishi Chemical Industries Limited | Alkylenedioxybenzene derivatives and acid addition salts thereof |
| JPS58154574A (ja) * | 1982-03-09 | 1983-09-14 | Mitsubishi Chem Ind Ltd | アルキレンジオキシベンゼン誘導体およびその酸付加塩 |
| US4569933A (en) * | 1984-04-13 | 1986-02-11 | Cornu Pierre Jean | Antihypertensive substituted derivatives of 2,5-diamino 1,4-diazole |
| CA1260474A (en) * | 1984-12-03 | 1989-09-26 | Raymond A. Stokbroekx | Benzoxazol- and benzothiazolamine derivatives |
| US4749702A (en) * | 1985-04-15 | 1988-06-07 | Janssen Pharmaceutica N. V. | Antidepressive substituted N-[(4-piperidinyl)alkyl] bicyclic condensed oxazol- and thiazolamines |
| DE3901814A1 (de) * | 1988-07-28 | 1990-02-01 | Bayer Ag | Substituierte aminomethylzetraline sowie ihre heterocyclischen analoga |
| FR2658823B1 (fr) * | 1990-02-27 | 1992-04-30 | Adir | Nouveaux derives d'aminomethylpiperidine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent . |
| US5182292A (en) * | 1991-06-21 | 1993-01-26 | American Home Products Corporation | Psychotropic piperidinylmethyl benzodioxans |
| FR2681325B1 (fr) * | 1991-09-16 | 1993-12-17 | Fabre Medicament Pierre | Derives de l'aminomethyl-4 piperidine, leur preparation et leur application en therapeutique. |
| SI9300097B (en) * | 1992-02-27 | 2001-12-31 | Janssen Pharmaceutica Nv | (benzodioxan, benzofuran or benzopyran) alkylamino) alkyl substituted guanidines |
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1993
- 1993-09-06 GB GB939318431A patent/GB9318431D0/en active Pending
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- 1994-09-01 ES ES94927531T patent/ES2144528T3/es not_active Expired - Lifetime
- 1994-09-01 UA UA96041333A patent/UA41952C2/uk unknown
- 1994-09-01 PL PL94313347A patent/PL178270B1/pl unknown
- 1994-09-01 KR KR1019960701111A patent/KR100325964B1/ko not_active IP Right Cessation
- 1994-09-01 CA CA002170056A patent/CA2170056A1/en not_active Abandoned
- 1994-09-01 EP EP94927531A patent/EP0717739B1/en not_active Expired - Lifetime
- 1994-09-01 SI SI9420058A patent/SI9420058B/sl unknown
- 1994-09-01 DE DE69423767T patent/DE69423767T2/de not_active Expired - Fee Related
- 1994-09-01 AU AU76928/94A patent/AU689802B2/en not_active Ceased
- 1994-09-01 BR BR9407413A patent/BR9407413A/pt not_active Application Discontinuation
- 1994-09-01 NZ NZ273581A patent/NZ273581A/en unknown
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- 1994-09-01 DK DK94927531T patent/DK0717739T3/da active
- 1994-09-01 CN CN94193808A patent/CN1052723C/zh not_active Expired - Fee Related
- 1994-09-01 AT AT94927531T patent/ATE191214T1/de not_active IP Right Cessation
- 1994-09-01 CZ CZ96614A patent/CZ61496A3/cs unknown
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- 1994-09-01 US US08/605,130 patent/US5767116A/en not_active Expired - Lifetime
- 1994-09-01 RU RU96113203A patent/RU2136680C1/ru active
- 1994-09-01 JP JP7508440A patent/JPH09502431A/ja not_active Ceased
- 1994-09-01 WO PCT/EP1994/002904 patent/WO1995007274A1/en not_active Application Discontinuation
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