UA79309C2 - Heterocyclic compounds - Google Patents

Heterocyclic compounds Download PDF

Info

Publication number: UA79309C2
Authority: UA; Ukraine
Prior art keywords: methanone; alkyl; benzoimidazol; methylpiperazin; methyl
Prior art date: 2002-09-06

Application number

UAA200503209A

Other languages

English (en)

Ukrainian (uk)

Original Assignee

Janssen Pharmaceutica Nv

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.)

2002-09-06

Filing date

2003-09-04

Publication date

2007-06-11

2003-09-04 Application filed by Janssen Pharmaceutica Nv filed Critical Janssen Pharmaceutica Nv

2007-06-11 Publication of UA79309C2 publication Critical patent/UA79309C2/uk

Links

150000002391 heterocyclic compounds Chemical class 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 111
125000001424 substituent group Chemical group 0.000 claims abstract description 19
238000011282 treatment Methods 0.000 claims abstract description 16
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 14
208000010668 atopic eczema Diseases 0.000 claims abstract description 5
230000000172 allergic effect Effects 0.000 claims abstract description 4
229910052717 sulfur Inorganic materials 0.000 claims abstract 3
125000000217 alkyl group Chemical group 0.000 claims description 56
229910052739 hydrogen Inorganic materials 0.000 claims description 52
-1 hydroxy, amino Chemical group 0.000 claims description 51
229910052799 carbon Inorganic materials 0.000 claims description 44
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 39
238000000034 method Methods 0.000 claims description 20
125000004433 nitrogen atom Chemical group N* 0.000 claims description 18
125000000753 cycloalkyl group Chemical group 0.000 claims description 17
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
229910052736 halogen Inorganic materials 0.000 claims description 16
150000002367 halogens Chemical class 0.000 claims description 16
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 15
229910052796 boron Inorganic materials 0.000 claims description 15
125000004093 cyano group Chemical group *C#N 0.000 claims description 15
125000005842 heteroatom Chemical group 0.000 claims description 15
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 13
229910052757 nitrogen Inorganic materials 0.000 claims description 11
208000035475 disorder Diseases 0.000 claims description 10
239000001257 hydrogen Substances 0.000 claims description 10
125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 10
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 10
125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 9
208000006673 asthma Diseases 0.000 claims description 9
230000001404 mediated effect Effects 0.000 claims description 9
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 9
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 9
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
206010039085 Rhinitis allergic Diseases 0.000 claims description 8
201000010105 allergic rhinitis Diseases 0.000 claims description 8
125000004571 thiomorpholin-4-yl group Chemical group N1(CCSCC1)* 0.000 claims description 8
125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 7
150000002148 esters Chemical class 0.000 claims description 7
150000003839 salts Chemical class 0.000 claims description 7
125000003545 alkoxy group Chemical group 0.000 claims description 6
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 6
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 6
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 6
239000003814 drug Substances 0.000 claims description 5
229910052740 iodine Inorganic materials 0.000 claims description 5
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 5
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
239000008194 pharmaceutical composition Substances 0.000 claims description 5
230000002265 prevention Effects 0.000 claims description 5
RHXSYTACTOMVLJ-UHFFFAOYSA-N 1H-benzimidazole-2-carboxylic acid Chemical compound C1=CC=C2NC(C(=O)O)=NC2=C1 RHXSYTACTOMVLJ-UHFFFAOYSA-N 0.000 claims description 4
125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 4
125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 4
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 description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
150000001721 carbon Chemical group 0.000 claims description 4
125000001309 chloro group Chemical group Cl* 0.000 claims description 4
229940079593 drug Drugs 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
208000027866 inflammatory disease Diseases 0.000 claims description 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
GKSPBWMLZIYREQ-UHFFFAOYSA-N (4-chloro-1h-benzimidazol-2-yl)-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C1=NC2=C(Cl)C=CC=C2N1 GKSPBWMLZIYREQ-UHFFFAOYSA-N 0.000 claims description 3
JQTLCZZJXYVAEB-UHFFFAOYSA-N (4-methyl-1h-benzimidazol-2-yl)-(3-methylpiperazin-1-yl)methanone Chemical compound C1CNC(C)CN1C(=O)C1=NC2=C(C)C=CC=C2N1 JQTLCZZJXYVAEB-UHFFFAOYSA-N 0.000 claims description 3
KCJHNHGIQWVNSS-UHFFFAOYSA-N (4-methyl-1h-benzimidazol-2-yl)-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C1=NC2=C(C)C=CC=C2N1 KCJHNHGIQWVNSS-UHFFFAOYSA-N 0.000 claims description 3
RURXHJWOGXWBLU-UHFFFAOYSA-N (4-methylpiperazin-1-yl)-[6-(trifluoromethyl)-1h-benzimidazol-2-yl]methanone Chemical compound C1CN(C)CCN1C(=O)C1=NC2=CC(C(F)(F)F)=CC=C2N1 RURXHJWOGXWBLU-UHFFFAOYSA-N 0.000 claims description 3
IRGAQXDRTLJBQB-UHFFFAOYSA-N (5,6-difluoro-1h-benzimidazol-2-yl)-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C1=NC2=CC(F)=C(F)C=C2N1 IRGAQXDRTLJBQB-UHFFFAOYSA-N 0.000 claims description 3
ZCDFRCAJGXZHBJ-UHFFFAOYSA-N 6-methyl-1h-benzimidazole-2-carboxylic acid Chemical compound CC1=CC=C2N=C(C(O)=O)NC2=C1 ZCDFRCAJGXZHBJ-UHFFFAOYSA-N 0.000 claims description 3
201000001320 Atherosclerosis Diseases 0.000 claims description 3
208000023275 Autoimmune disease Diseases 0.000 claims description 3
PSKWCTYZMXFVDK-UHFFFAOYSA-N [2-(4-methylpiperazine-1-carbonyl)-3h-benzimidazol-5-yl]-phenylmethanone Chemical compound C1CN(C)CCN1C(=O)C1=NC2=CC(C(=O)C=3C=CC=CC=3)=CC=C2N1 PSKWCTYZMXFVDK-UHFFFAOYSA-N 0.000 claims description 3
229910052801 chlorine Inorganic materials 0.000 claims description 3
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
206010039073 rheumatoid arthritis Diseases 0.000 claims description 3
KVHNNAFIEYQJFP-UHFFFAOYSA-N (4-amino-1h-benzimidazol-2-yl)-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C1=NC2=C(N)C=CC=C2N1 KVHNNAFIEYQJFP-UHFFFAOYSA-N 0.000 claims description 2
OYCPMRKNILHXGZ-UHFFFAOYSA-N (4-ethylpiperazin-1-yl)-(4-methyl-1h-benzimidazol-2-yl)methanone Chemical compound C1CN(CC)CCN1C(=O)C1=NC2=C(C)C=CC=C2N1 OYCPMRKNILHXGZ-UHFFFAOYSA-N 0.000 claims description 2
SJSFVUFHKYUAIF-UHFFFAOYSA-N (4-methyl-1,3-benzoxazol-2-yl)-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C1=NC2=C(C)C=CC=C2O1 SJSFVUFHKYUAIF-UHFFFAOYSA-N 0.000 claims description 2
QGHMMSSRSVVVRM-UHFFFAOYSA-N (4-methyl-1h-benzimidazol-2-yl)-piperazin-1-ylmethanone Chemical compound N=1C=2C(C)=CC=CC=2NC=1C(=O)N1CCNCC1 QGHMMSSRSVVVRM-UHFFFAOYSA-N 0.000 claims description 2
UBKBDXQCADGBAU-UHFFFAOYSA-N (4-methylpiperazin-1-yl)-[4-(propan-2-ylamino)-1h-benzimidazol-2-yl]methanone Chemical compound N=1C=2C(NC(C)C)=CC=CC=2NC=1C(=O)N1CCN(C)CC1 UBKBDXQCADGBAU-UHFFFAOYSA-N 0.000 claims description 2
UHYCZMGQTVNZIL-UHFFFAOYSA-N (5,6-difluoro-1h-benzimidazol-2-yl)-(3-methylpiperazin-1-yl)methanone Chemical compound C1CNC(C)CN1C(=O)C1=NC2=CC(F)=C(F)C=C2N1 UHYCZMGQTVNZIL-UHFFFAOYSA-N 0.000 claims description 2
KQCYNSQKCRQOBH-UHFFFAOYSA-N (5,6-difluoro-1h-benzimidazol-2-yl)-(4-ethylpiperazin-1-yl)methanone Chemical compound C1CN(CC)CCN1C(=O)C1=NC2=CC(F)=C(F)C=C2N1 KQCYNSQKCRQOBH-UHFFFAOYSA-N 0.000 claims description 2
JVXIJSYPRSOIMJ-UHFFFAOYSA-N (7-methyl-1,3-benzoxazol-2-yl)-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C1=NC2=CC=CC(C)=C2O1 JVXIJSYPRSOIMJ-UHFFFAOYSA-N 0.000 claims description 2
GTPFOQVEOMZTQO-UHFFFAOYSA-N 1,3-benzothiazol-2-yl-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C1=NC2=CC=CC=C2S1 GTPFOQVEOMZTQO-UHFFFAOYSA-N 0.000 claims description 2
ZMYZAIFGDZEZEJ-UHFFFAOYSA-N 1,3-benzoxazol-2-yl-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C1=NC2=CC=CC=C2O1 ZMYZAIFGDZEZEJ-UHFFFAOYSA-N 0.000 claims description 2
OBQMQANOQQJNFK-UHFFFAOYSA-N 4-methyl-1h-benzimidazole-2-carboxylic acid Chemical compound CC1=CC=CC2=C1N=C(C(O)=O)N2 OBQMQANOQQJNFK-UHFFFAOYSA-N 0.000 claims description 2
VVCCUBBNXURKEE-UHFFFAOYSA-N 5,6-difluoro-1h-benzimidazole-2-carboxylic acid Chemical compound FC1=C(F)C=C2NC(C(=O)O)=NC2=C1 VVCCUBBNXURKEE-UHFFFAOYSA-N 0.000 claims description 2
TYXHLKWWJIWESF-UHFFFAOYSA-N 6-fluoro-1h-benzimidazole-2-carboxylic acid Chemical compound C1=C(F)C=C2NC(C(=O)O)=NC2=C1 TYXHLKWWJIWESF-UHFFFAOYSA-N 0.000 claims description 2
206010009900 Colitis ulcerative Diseases 0.000 claims description 2
208000011231 Crohn disease Diseases 0.000 claims description 2
208000029462 Immunodeficiency disease Diseases 0.000 claims description 2
208000022559 Inflammatory bowel disease Diseases 0.000 claims description 2
208000018501 Lymphatic disease Diseases 0.000 claims description 2
201000004681 Psoriasis Diseases 0.000 claims description 2
201000006704 Ulcerative Colitis Diseases 0.000 claims description 2
125000001153 fluoro group Chemical group F* 0.000 claims description 2
125000000623 heterocyclic group Chemical group 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims description 2
125000002632 imidazolidinyl group Chemical group 0.000 claims description 2
208000018555 lymphatic system disease Diseases 0.000 claims description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
125000002757 morpholinyl group Chemical group 0.000 claims description 2
201000006417 multiple sclerosis Diseases 0.000 claims description 2
125000004193 piperazinyl group Chemical group 0.000 claims description 2
125000003386 piperidinyl group Chemical group 0.000 claims description 2
125000003072 pyrazolidinyl group Chemical group 0.000 claims description 2
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 2
125000004568 thiomorpholinyl group Chemical group 0.000 claims description 2
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
XFOCDCVVEXCWCX-UHFFFAOYSA-N (4,5-dimethyl-1h-benzimidazol-2-yl)-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C1=NC2=C(C)C(C)=CC=C2N1 XFOCDCVVEXCWCX-UHFFFAOYSA-N 0.000 claims 1
FJVRPDNNLDYOPB-UHFFFAOYSA-N (4,6-difluoro-1h-benzimidazol-2-yl)-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C1=NC2=C(F)C=C(F)C=C2N1 FJVRPDNNLDYOPB-UHFFFAOYSA-N 0.000 claims 1
GYYBQBFFXKJAFU-UHFFFAOYSA-N (4-ethylpiperazin-1-yl)-(6-fluoro-1h-benzimidazol-2-yl)methanone Chemical compound C1CN(CC)CCN1C(=O)C1=NC2=CC(F)=CC=C2N1 GYYBQBFFXKJAFU-UHFFFAOYSA-N 0.000 claims 1
DTXHWDXBLANYOU-UHFFFAOYSA-N (4-methylpiperazin-1-yl)-(4-nitro-1h-benzimidazol-2-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C1=NC2=C([N+]([O-])=O)C=CC=C2N1 DTXHWDXBLANYOU-UHFFFAOYSA-N 0.000 claims 1
CMBIJPNSXFXCIW-UHFFFAOYSA-N (4-methylpiperazin-1-yl)-(6-nitro-1h-benzimidazol-2-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C1=NC2=CC([N+]([O-])=O)=CC=C2N1 CMBIJPNSXFXCIW-UHFFFAOYSA-N 0.000 claims 1
DLODBVBWYZQNMJ-UHFFFAOYSA-N (4-methylpiperazin-1-yl)-[5-(trifluoromethoxy)-1,3-benzoxazol-2-yl]methanone Chemical compound C1CN(C)CCN1C(=O)C1=NC2=CC(OC(F)(F)F)=CC=C2O1 DLODBVBWYZQNMJ-UHFFFAOYSA-N 0.000 claims 1
QXOOYTVOPSQVHZ-UHFFFAOYSA-N (4-methylpiperazin-1-yl)-[5-(trifluoromethyl)-1,3-benzothiazol-2-yl]methanone Chemical compound C1CN(C)CCN1C(=O)C1=NC2=CC(C(F)(F)F)=CC=C2S1 QXOOYTVOPSQVHZ-UHFFFAOYSA-N 0.000 claims 1
LCVQWNHJNCLEFE-UHFFFAOYSA-N (5,6-dichloro-1h-benzimidazol-2-yl)-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C1=NC2=CC(Cl)=C(Cl)C=C2N1 LCVQWNHJNCLEFE-UHFFFAOYSA-N 0.000 claims 1
VGDHTVNHYVEPID-UHFFFAOYSA-N (5,6-dimethyl-1h-benzimidazol-2-yl)-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C1=NC2=CC(C)=C(C)C=C2N1 VGDHTVNHYVEPID-UHFFFAOYSA-N 0.000 claims 1
DPPNIYJDZSKSIQ-UHFFFAOYSA-N (5,7-difluoro-1,3-benzoxazol-2-yl)-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C1=NC2=CC(F)=CC(F)=C2O1 DPPNIYJDZSKSIQ-UHFFFAOYSA-N 0.000 claims 1
IAQXXQRUVZLWRM-UHFFFAOYSA-N (5-chloro-1,3-benzothiazol-2-yl)-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C1=NC2=CC(Cl)=CC=C2S1 IAQXXQRUVZLWRM-UHFFFAOYSA-N 0.000 claims 1
MCFJROXHMJOJDE-UHFFFAOYSA-N (6-bromo-1h-benzimidazol-2-yl)-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C1=NC2=CC(Br)=CC=C2N1 MCFJROXHMJOJDE-UHFFFAOYSA-N 0.000 claims 1
206010028980 Neoplasm Diseases 0.000 claims 1
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239000003623 enhancer Substances 0.000 claims 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims 1
238000012876 topography Methods 0.000 claims 1
229910052760 oxygen Inorganic materials 0.000 abstract description 4
239000003396 histamine H4 receptor antagonist Substances 0.000 abstract description 2
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125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 2
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JXFUAAOZEBNUNM-UHFFFAOYSA-N (5-chloro-6-methyl-1h-benzimidazol-2-yl)-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C1=NC2=CC(Cl)=C(C)C=C2N1 JXFUAAOZEBNUNM-UHFFFAOYSA-N 0.000 description 6
CTBHTPQCCMGLKI-UHFFFAOYSA-N 4-methyl-2-(trichloromethyl)-1h-benzimidazole Chemical compound CC1=CC=CC2=C1N=C(C(Cl)(Cl)Cl)N2 CTBHTPQCCMGLKI-UHFFFAOYSA-N 0.000 description 6
GNKRJZXKNZQBJQ-UHFFFAOYSA-N 5,6-difluoro-2-(trichloromethyl)-1h-benzimidazole Chemical compound C1=C(F)C(F)=CC2=C1NC(C(Cl)(Cl)Cl)=N2 GNKRJZXKNZQBJQ-UHFFFAOYSA-N 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
OHCQJHSOBUTRHG-KGGHGJDLSA-N FORSKOLIN Chemical compound O=C([C@@]12O)C[C@](C)(C=C)O[C@]1(C)[C@@H](OC(=O)C)[C@@H](O)[C@@H]1[C@]2(C)[C@@H](O)CCC1(C)C OHCQJHSOBUTRHG-KGGHGJDLSA-N 0.000 description 6
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles 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 in position 2
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- 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
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
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UAA200503209A 2002-09-06 2003-09-04 Heterocyclic compounds UA79309C2 (en)

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PCT/US2003/027461 WO2004022060A2 (en)	2002-09-06	2003-09-04	(1h-benzoimidazol-2-yl)-(piperazinyl)-methanone derivatives and related compounds as histamine h4-receptor antagonists for the treatment of inflammatory and allergic disorders

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EP (1)	EP1545532A2 (pl)
JP (1)	JP2006500390A (pl)
KR (1)	KR20050033662A (pl)
CN (1)	CN1694704A (pl)
AR (1)	AR041170A1 (pl)
AU (1)	AU2003265886A1 (pl)
BR (1)	BR0314059A (pl)
CA (1)	CA2497827A1 (pl)
EC (1)	ECSP055647A (pl)
IS (1)	IS7716A (pl)
MX (1)	MXPA05002575A (pl)
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NZ (1)	NZ538401A (pl)
PL (1)	PL377087A1 (pl)
RS (1)	RS20050201A (pl)
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UA (1)	UA79309C2 (pl)
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AU2001241927A1 (en)	2000-02-28	2001-09-12	Scios Inc.	Inhibitors of p38-alpha kinase
TWI288745B (en)	2000-04-05	2007-10-21	Daiichi Seiyaku Co	Ethylenediamine derivatives
JP2003104975A (ja) *	2001-09-28	2003-04-09	Sumitomo Pharmaceut Co Ltd	新規なベンゾチアゾール化合物

2003
- 2003-09-04 MX MXPA05002575A patent/MXPA05002575A/es unknown
- 2003-09-04 US US10/655,381 patent/US7504426B2/en not_active Expired - Lifetime
- 2003-09-04 RU RU2005106274/04A patent/RU2005106274A/ru not_active Application Discontinuation
- 2003-09-04 CN CNA038249693A patent/CN1694704A/zh active Pending
- 2003-09-04 RS YUP-2005/0201A patent/RS20050201A/sr unknown
- 2003-09-04 CA CA002497827A patent/CA2497827A1/en not_active Abandoned
- 2003-09-04 AU AU2003265886A patent/AU2003265886A1/en not_active Abandoned
- 2003-09-04 UA UAA200503209A patent/UA79309C2/uk unknown
- 2003-09-04 EP EP03794573A patent/EP1545532A2/en not_active Withdrawn
- 2003-09-04 KR KR1020057003818A patent/KR20050033662A/ko not_active Withdrawn
- 2003-09-04 WO PCT/US2003/027461 patent/WO2004022060A2/en not_active Ceased
- 2003-09-04 NZ NZ538401A patent/NZ538401A/en unknown
- 2003-09-04 PL PL377087A patent/PL377087A1/pl not_active Application Discontinuation
- 2003-09-04 BR BR0314059-8A patent/BR0314059A/pt not_active IP Right Cessation
- 2003-09-04 JP JP2004534443A patent/JP2006500390A/ja not_active Withdrawn
- 2003-09-05 AR ARP030103235A patent/AR041170A1/es not_active Application Discontinuation
2005
- 2005-02-24 IS IS7716A patent/IS7716A/is unknown
- 2005-03-04 EC EC2005005647A patent/ECSP055647A/es unknown
- 2005-04-05 NO NO20051694A patent/NO20051694L/no not_active Application Discontinuation
- 2005-04-05 ZA ZA200502750A patent/ZA200502750B/en unknown

Also Published As

Publication number	Publication date
RS20050201A (sr)	2007-06-04
JP2006500390A (ja)	2006-01-05
RU2005106274A (ru)	2005-11-10
WO2004022060A8 (en)	2004-06-03
PL377087A1 (pl)	2006-01-23
NO20051694L (no)	2005-04-05
US20040058934A1 (en)	2004-03-25
WO2004022060A3 (en)	2004-07-08
KR20050033662A (ko)	2005-04-12
MXPA05002575A (es)	2005-09-08
ZA200502750B (en)	2006-06-28
AR041170A1 (es)	2005-05-04
NZ538401A (en)	2008-03-28
WO2004022060A2 (en)	2004-03-18
CA2497827A1 (en)	2004-03-18
AU2003265886A1 (en)	2004-03-29
EP1545532A2 (en)	2005-06-29
ECSP055647A (es)	2005-05-30
IS7716A (is)	2005-02-24
BR0314059A (pt)	2005-07-05
CN1694704A (zh)	2005-11-09
US7504426B2 (en)	2009-03-17

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