BG103754A - Заместени 4-арилметилен-2-имино-2,3-дихидротиазоли, техни производни и използването им във фармацията - Google Patents

Заместени 4-арилметилен-2-имино-2,3-дихидротиазоли, техни производни и използването им във фармацията Download PDF

Info

Publication number: BG103754A
Authority: BG; Bulgaria
Prior art keywords: dihydrothiazole; cyclobutyl; carbon atoms; dichlorophenyl; optionally substituted
Prior art date: 1997-03-15

Application number

BG103754A

Other languages

Bulgarian (bg)

English (en)

Inventor

Sharon Cheetham

Frank Kerrigan

Colin Jones

Original Assignee

Knoll Gmbh

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.)

1997-03-15

Filing date

1999-09-24

Publication date

2000-06-30

1999-09-24 Application filed by Knoll Gmbh filed Critical Knoll Gmbh

2000-06-30 Publication of BG103754A publication Critical patent/BG103754A/bg

Links

150000001875 compounds Chemical class 0.000 claims abstract description 159
239000000203 mixture Substances 0.000 claims abstract description 118
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 97
-1 benzo(b)thiophenyl Chemical group 0.000 claims abstract description 77
125000000217 alkyl group Chemical group 0.000 claims abstract description 47
125000003118 aryl group Chemical group 0.000 claims abstract description 23
238000000034 method Methods 0.000 claims abstract description 23
125000004429 atom Chemical group 0.000 claims abstract description 22
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 22
125000001072 heteroaryl group Chemical group 0.000 claims abstract description 18
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 abstract description 16
150000003839 salts Chemical class 0.000 claims abstract description 16
125000001624 naphthyl group Chemical group 0.000 claims abstract description 13
238000002360 preparation method Methods 0.000 claims abstract description 12
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 10
125000002947 alkylene group Chemical group 0.000 claims abstract description 9
208000012902 Nervous system disease Diseases 0.000 claims abstract description 8
208000025966 Neurological disease Diseases 0.000 claims abstract description 8
208000020401 Depressive disease Diseases 0.000 claims abstract description 7
125000003342 alkenyl group Chemical group 0.000 claims abstract description 6
125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 6
125000004446 heteroarylalkyl group Chemical group 0.000 claims abstract description 6
125000005002 aryl methyl group Chemical group 0.000 claims abstract description 5
125000004981 cycloalkylmethyl group Chemical group 0.000 claims abstract description 5
125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract description 4
125000005843 halogen group Chemical group 0.000 claims description 61
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 39
125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 37
150000002367 halogens Chemical class 0.000 claims description 36
229910052736 halogen Inorganic materials 0.000 claims description 35
125000001424 substituent group Chemical group 0.000 claims description 25
125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 22
125000003545 alkoxy group Chemical group 0.000 claims description 21
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 17
125000004414 alkyl thio group Chemical group 0.000 claims description 17
229910052739 hydrogen Inorganic materials 0.000 claims description 14
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 14
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
OYJGEOAXBALSMM-UHFFFAOYSA-N 2,3-dihydro-1,3-thiazole Chemical compound C1NC=CS1 OYJGEOAXBALSMM-UHFFFAOYSA-N 0.000 claims description 10
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 10
239000001257 hydrogen Substances 0.000 claims description 9
239000008194 pharmaceutical composition Substances 0.000 claims description 9
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 8
206010010904 Convulsion Diseases 0.000 claims description 7
208000027089 Parkinsonian disease Diseases 0.000 claims description 7
206010034010 Parkinsonism Diseases 0.000 claims description 7
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 7
239000002253 acid Substances 0.000 claims description 6
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
239000004090 neuroprotective agent Substances 0.000 claims description 6
229910052799 carbon Inorganic materials 0.000 claims description 5
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 5
230000002265 prevention Effects 0.000 claims description 5
125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 4
RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 4
239000003814 drug Substances 0.000 claims description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
239000003085 diluting agent Substances 0.000 claims description 3
125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 3
XHBLOTICYAEWOZ-UHFFFAOYSA-N 3-[1-(3,4-dichlorophenyl)cyclobutyl]-5-methyl-5,6-dihydroimidazo[2,1-b][1,3]thiazole Chemical compound N12C(C)CN=C2SC=C1C1(C=2C=C(Cl)C(Cl)=CC=2)CCC1 XHBLOTICYAEWOZ-UHFFFAOYSA-N 0.000 claims description 2
KILNDGCEQXIIJU-UHFFFAOYSA-N 3-[1-(3-fluorophenyl)cyclobutyl]-5,6-dihydroimidazo[2,1-b][1,3]thiazole Chemical compound FC1=CC=CC(C2(CCC2)C=2N3CCN=C3SC=2)=C1 KILNDGCEQXIIJU-UHFFFAOYSA-N 0.000 claims description 2
OGIHLNAIOATGSR-UHFFFAOYSA-N 3-[1-(4-methylsulfanylphenyl)cyclobutyl]-5,6-dihydroimidazo[2,1-b][1,3]thiazole Chemical compound C1=CC(SC)=CC=C1C1(C=2N3CCN=C3SC=2)CCC1 OGIHLNAIOATGSR-UHFFFAOYSA-N 0.000 claims description 2
PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 claims description 2
125000004122 cyclic group Chemical group 0.000 claims description 2
DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims description 2
YABJLYQVPIPDMA-UHFFFAOYSA-N n,3-bis(4-ethoxyphenyl)-4-(1-naphthalen-2-ylcyclobutyl)-1,3-thiazol-2-imine Chemical compound C1=CC(OCC)=CC=C1N=C1N(C=2C=CC(OCC)=CC=2)C(C2(CCC2)C=2C=C3C=CC=CC3=CC=2)=CS1 YABJLYQVPIPDMA-UHFFFAOYSA-N 0.000 claims description 2
CONIZJYXKKRKSS-UHFFFAOYSA-N n,3-dicyclopentyl-4-(1-naphthalen-2-ylcyclobutyl)-1,3-thiazol-2-imine Chemical compound C1CCC1(C=1C=C2C=CC=CC2=CC=1)C(N1C2CCCC2)=CSC1=NC1CCCC1 CONIZJYXKKRKSS-UHFFFAOYSA-N 0.000 claims description 2
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 2
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 2
KNEDPNIYOJPCTK-UHFFFAOYSA-N 4-[1-(3,4-dichlorophenyl)cyclobutyl]-n,3-bis(2-phenylethyl)-1,3-thiazol-2-imine Chemical compound C1=C(Cl)C(Cl)=CC=C1C1(C=2N(C(=NCCC=3C=CC=CC=3)SC=2)CCC=2C=CC=CC=2)CCC1 KNEDPNIYOJPCTK-UHFFFAOYSA-N 0.000 claims 1
OIQFPGHUVXLXCX-UHFFFAOYSA-N 4-[1-(3,4-dichlorophenyl)cyclobutyl]-n,3-dipropyl-1,3-thiazol-2-imine Chemical compound CCCN1C(=NCCC)SC=C1C1(C=2C=C(Cl)C(Cl)=CC=2)CCC1 OIQFPGHUVXLXCX-UHFFFAOYSA-N 0.000 claims 1
XPOSGVNDXZZZCC-UHFFFAOYSA-N 4-[1-(4-chlorophenyl)cyclopentyl]-n,3-bis[2-(3,4-dimethoxyphenyl)ethyl]-1,3-thiazol-2-imine Chemical compound C1=C(OC)C(OC)=CC=C1CCN=C1N(CCC=2C=C(OC)C(OC)=CC=2)C(C2(CCCC2)C=2C=CC(Cl)=CC=2)=CS1 XPOSGVNDXZZZCC-UHFFFAOYSA-N 0.000 claims 1
DINXQSYNWHLKSS-UHFFFAOYSA-N n,3-bis[2-(3,4-dimethoxyphenyl)ethyl]-4-(1-naphthalen-2-ylcyclobutyl)-1,3-thiazol-2-imine Chemical compound C1=C(OC)C(OC)=CC=C1CCN=C1N(CCC=2C=C(OC)C(OC)=CC=2)C(C2(CCC2)C=2C=C3C=CC=CC3=CC=2)=CS1 DINXQSYNWHLKSS-UHFFFAOYSA-N 0.000 claims 1
OKQDCONLUFMRRB-UHFFFAOYSA-N n,3-dibutyl-4-[2-(3,4-dichlorophenyl)propan-2-yl]-1,3-thiazol-2-imine Chemical compound CCCCN1C(=NCCCC)SC=C1C(C)(C)C1=CC=C(Cl)C(Cl)=C1 OKQDCONLUFMRRB-UHFFFAOYSA-N 0.000 claims 1
JTJMJGYZQZDUJJ-UHFFFAOYSA-N phencyclidine Chemical class C1CCCCN1C1(C=2C=CC=CC=2)CCCCC1 JTJMJGYZQZDUJJ-UHFFFAOYSA-N 0.000 claims 1
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims 1
125000000547 substituted alkyl group Chemical group 0.000 abstract description 5
208000019901 Anxiety disease Diseases 0.000 abstract 1
230000036506 anxiety Effects 0.000 abstract 1
230000000324 neuroprotective effect Effects 0.000 abstract 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 126
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 97
238000004128 high performance liquid chromatography Methods 0.000 description 70
239000000243 solution Substances 0.000 description 65
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 55
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 54
239000002904 solvent Substances 0.000 description 51
239000007787 solid Substances 0.000 description 47
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 39
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 36
QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 36
238000003756 stirring Methods 0.000 description 32
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 30
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 25
238000010992 reflux Methods 0.000 description 25
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 24
239000003921 oil Substances 0.000 description 22
235000019198 oils Nutrition 0.000 description 22
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
230000027455 binding Effects 0.000 description 21
239000000047 product Substances 0.000 description 20
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 18
229960003638 dopamine Drugs 0.000 description 18
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 17
239000008187 granular material Substances 0.000 description 16
239000003446 ligand Substances 0.000 description 16
238000012360 testing method Methods 0.000 description 16
SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 14
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
239000000284 extract Substances 0.000 description 14
238000001914 filtration Methods 0.000 description 14
229960002748 norepinephrine Drugs 0.000 description 14
SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 14
239000003826 tablet Substances 0.000 description 14
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 13
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 13
229910052794 bromium Inorganic materials 0.000 description 13
229920006395 saturated elastomer Polymers 0.000 description 13
239000007788 liquid Substances 0.000 description 12
229910052943 magnesium sulfate Inorganic materials 0.000 description 12
235000019341 magnesium sulphate Nutrition 0.000 description 12
239000012299 nitrogen atmosphere Substances 0.000 description 12
230000009870 specific binding Effects 0.000 description 12
239000000725 suspension Substances 0.000 description 12
238000009835 boiling Methods 0.000 description 11
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
PDQAZBWRQCGBEV-UHFFFAOYSA-N Ethylenethiourea Chemical compound S=C1NCCN1 PDQAZBWRQCGBEV-UHFFFAOYSA-N 0.000 description 10
238000000746 purification Methods 0.000 description 10
239000011780 sodium chloride Substances 0.000 description 10
239000012839 Krebs-Henseleit buffer Substances 0.000 description 9
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
239000007983 Tris buffer Substances 0.000 description 9
239000002775 capsule Substances 0.000 description 9
210000004027 cell Anatomy 0.000 description 9
235000017557 sodium bicarbonate Nutrition 0.000 description 9
229910000030 sodium bicarbonate Inorganic materials 0.000 description 9
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 9
WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 8
238000000338 in vitro Methods 0.000 description 8
230000009871 nonspecific binding Effects 0.000 description 8
239000006228 supernatant Substances 0.000 description 8
NWABWFPZIMWXHT-UHFFFAOYSA-N 2,3-dihydro-1,3-thiazole;hydrobromide Chemical compound Br.C1NC=CS1 NWABWFPZIMWXHT-UHFFFAOYSA-N 0.000 description 7
229930006000 Sucrose Natural products 0.000 description 7
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 7
210000005013 brain tissue Anatomy 0.000 description 7
238000005119 centrifugation Methods 0.000 description 7
239000003208 petroleum Substances 0.000 description 7
239000000377 silicon dioxide Substances 0.000 description 7
239000005720 sucrose Substances 0.000 description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 6
239000013543 active substance Substances 0.000 description 6
239000003480 eluent Substances 0.000 description 6
238000003818 flash chromatography Methods 0.000 description 6
239000011777 magnesium Substances 0.000 description 6
229910052749 magnesium Inorganic materials 0.000 description 6
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
239000012528 membrane Substances 0.000 description 6
239000002699 waste material Substances 0.000 description 6
DDGHBOLOCQWPKE-UHFFFAOYSA-N 1,3-thiazole;hydrobromide Chemical compound [Br-].C1=CSC=[NH+]1 DDGHBOLOCQWPKE-UHFFFAOYSA-N 0.000 description 5
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
230000008878 coupling Effects 0.000 description 5
238000010168 coupling process Methods 0.000 description 5
238000005859 coupling reaction Methods 0.000 description 5
238000009472 formulation Methods 0.000 description 5
VXWPONVCMVLXBW-UHFFFAOYSA-M magnesium;carbanide;iodide Chemical compound [CH3-].[Mg+2].[I-] VXWPONVCMVLXBW-UHFFFAOYSA-M 0.000 description 5
238000001819 mass spectrum Methods 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
229910052938 sodium sulfate Inorganic materials 0.000 description 5
235000011152 sodium sulphate Nutrition 0.000 description 5
239000000829 suppository Substances 0.000 description 5
CTKUIZGFDSJHPY-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)cyclobutane-1-carbonitrile Chemical compound C1=C(Cl)C(Cl)=CC=C1C1(C#N)CCC1 CTKUIZGFDSJHPY-UHFFFAOYSA-N 0.000 description 4
QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 4
GDLAAGCDLYXWCK-UHFFFAOYSA-N 2-bromo-1-[1-(3,4-dichlorophenyl)cyclobutyl]ethanone Chemical compound C1=C(Cl)C(Cl)=CC=C1C1(C(=O)CBr)CCC1 GDLAAGCDLYXWCK-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
241000700159 Rattus Species 0.000 description 4
125000001246 bromo group Chemical group Br* 0.000 description 4
125000001309 chloro group Chemical group Cl* 0.000 description 4
230000001054 cortical effect Effects 0.000 description 4
206010015037 epilepsy Diseases 0.000 description 4
239000012530 fluid Substances 0.000 description 4
239000003701 inert diluent Substances 0.000 description 4
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239000001103 potassium chloride Substances 0.000 description 4
235000011164 potassium chloride Nutrition 0.000 description 4
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 4
238000005303 weighing Methods 0.000 description 4
125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 description 3
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UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 3
229920000623 Cellulose acetate phthalate Polymers 0.000 description 3
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
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238000000576 coating method Methods 0.000 description 3
229940125773 compound 10 Drugs 0.000 description 3
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239000012153 distilled water Substances 0.000 description 3
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NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
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QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/10—Spiro-condensed systems
- 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
- 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
- A61P25/08—Antiepileptics; Anticonvulsants
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
- 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
- A61P25/22—Anxiolytics
- 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
- A61P25/24—Antidepressants
- 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity 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
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/38—Nitrogen atoms
- C07D277/42—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Biomedical Technology (AREA)
Neurosurgery (AREA)
Neurology (AREA)
Psychiatry (AREA)
Pain & Pain Management (AREA)
Hospice & Palliative Care (AREA)
Diabetes (AREA)
Psychology (AREA)
Hematology (AREA)
Child & Adolescent Psychology (AREA)
Obesity (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Thiazole And Isothizaole Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Steroid Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Plural Heterocyclic Compounds (AREA)

BG103754A 1997-03-15 1999-09-24 Заместени 4-арилметилен-2-имино-2,3-дихидротиазоли, техни производни и използването им във фармацията BG103754A (bg)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GBGB9705428.2A GB9705428D0 (en)	1997-03-15	1997-03-15	Therapeutic agents
PCT/EP1998/001358 WO1998041528A1 (en)	1997-03-15	1998-03-09	Substituted 4-arylmethylene-2-imino-2,3-dihydrothiazoles and derivatives and their pharmaceutical use

Publications (1)

Publication Number	Publication Date
BG103754A true BG103754A (bg)	2000-06-30

Family

ID=10809320

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BG103754A BG103754A (bg)	1997-03-15	1999-09-24	Заместени 4-арилметилен-2-имино-2,3-дихидротиазоли, техни производни и използването им във фармацията

Country Status (22)

Country	Link
US (1)	US6187802B1 (de)
EP (1)	EP0970090B1 (de)
JP (1)	JP2001515501A (de)
KR (1)	KR20000076190A (de)
CN (1)	CN1255136A (de)
AT (1)	ATE218573T1 (de)
AU (1)	AU6728898A (de)
BG (1)	BG103754A (de)
BR (1)	BR9808254A (de)
CA (1)	CA2283438A1 (de)
DE (1)	DE69805781D1 (de)
GB (1)	GB9705428D0 (de)
HU (1)	HUP0001508A3 (de)
ID (1)	ID22636A (de)
IL (1)	IL131515A0 (de)
NO (1)	NO994452L (de)
NZ (1)	NZ337378A (de)
PL (1)	PL335696A1 (de)
SK (1)	SK122099A3 (de)
TR (1)	TR199902291T2 (de)
WO (1)	WO1998041528A1 (de)
ZA (1)	ZA982134B (de)

Families Citing this family (37)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE19856965A1 (de) *	1998-12-10	2000-06-15	Bayer Ag	Substituierte 2-Imino-thiazoline
AU3894500A (en)	1999-03-19	2000-10-09	Knoll Pharmaceutical Company	Prevention of cardiovascular disease
WO2000056309A1 (en)	1999-03-19	2000-09-28	Knoll Pharmaceutical Company	Method of treating sexual dysfunction
AU3895300A (en)	1999-03-19	2000-10-09	Knoll Pharmaceutical Company	Treatment of chronic fatigue syndrome
US6365632B1 (en)	1999-03-19	2002-04-02	Knoll Pharmaceuticals Company	Treatment of orthostatic hypotension
WO2000056321A1 (en)	1999-03-19	2000-09-28	Knoll Pharmaceutical Company	Treatment of hyperactivity disorders
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1997
- 1997-03-15 GB GBGB9705428.2A patent/GB9705428D0/en active Pending
1998
- 1998-03-09 NZ NZ337378A patent/NZ337378A/xx unknown
- 1998-03-09 US US09/380,967 patent/US6187802B1/en not_active Expired - Fee Related
- 1998-03-09 JP JP54009198A patent/JP2001515501A/ja active Pending
- 1998-03-09 PL PL98335696A patent/PL335696A1/xx unknown
- 1998-03-09 CN CN98804891A patent/CN1255136A/zh active Pending
- 1998-03-09 HU HU0001508A patent/HUP0001508A3/hu unknown
- 1998-03-09 AU AU67288/98A patent/AU6728898A/en not_active Abandoned
- 1998-03-09 ID IDW991023A patent/ID22636A/id unknown
- 1998-03-09 CA CA002283438A patent/CA2283438A1/en not_active Abandoned
- 1998-03-09 IL IL13151598A patent/IL131515A0/xx unknown
- 1998-03-09 WO PCT/EP1998/001358 patent/WO1998041528A1/en not_active Ceased
- 1998-03-09 AT AT98912459T patent/ATE218573T1/de not_active IP Right Cessation
- 1998-03-09 SK SK1220-99A patent/SK122099A3/sk unknown
- 1998-03-09 KR KR1019997008284A patent/KR20000076190A/ko not_active Withdrawn
- 1998-03-09 EP EP98912459A patent/EP0970090B1/de not_active Expired - Lifetime
- 1998-03-09 BR BR9808254-0A patent/BR9808254A/pt not_active IP Right Cessation
- 1998-03-09 DE DE69805781T patent/DE69805781D1/de not_active Expired - Lifetime
- 1998-03-09 TR TR1999/02291T patent/TR199902291T2/xx unknown
- 1998-03-13 ZA ZA9802134A patent/ZA982134B/xx unknown
1999
- 1999-09-14 NO NO994452A patent/NO994452L/no unknown
- 1999-09-24 BG BG103754A patent/BG103754A/bg unknown

Also Published As

Publication number	Publication date
CA2283438A1 (en)	1998-09-24
GB9705428D0 (en)	1997-04-30
NO994452D0 (no)	1999-09-14
WO1998041528A1 (en)	1998-09-24
PL335696A1 (en)	2000-05-08
ATE218573T1 (de)	2002-06-15
IL131515A0 (en)	2001-01-28
SK122099A3 (en)	2000-05-16
ID22636A (id)	1999-12-02
DE69805781D1 (de)	2002-07-11
EP0970090B1 (de)	2002-06-05
HUP0001508A2 (hu)	2001-01-29
KR20000076190A (ko)	2000-12-26
US6187802B1 (en)	2001-02-13
EP0970090A1 (de)	2000-01-12
JP2001515501A (ja)	2001-09-18
HUP0001508A3 (en)	2003-01-28
NZ337378A (en)	2001-01-26
AU6728898A (en)	1998-10-12
CN1255136A (zh)	2000-05-31
TR199902291T2 (xx)	1999-12-21
NO994452L (no)	1999-09-14
ZA982134B (en)	1999-09-13
BR9808254A (pt)	2000-05-16

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JP2006508113A (ja)	2006-03-09	キノリン誘導体
CZ9903260A3 (cs)	2000-11-15	Terapeutická činidla
MXPA97009509A (en)	1998-10-15	Therapeutic agents