WO1995014007B1 - Phenyl-alkyl imidazoles as h3-receptor antagonists - Google Patents
Phenyl-alkyl imidazoles as h3-receptor antagonistsInfo
- Publication number
- WO1995014007B1 WO1995014007B1 PCT/US1994/012717 US9412717W WO9514007B1 WO 1995014007 B1 WO1995014007 B1 WO 1995014007B1 US 9412717 W US9412717 W US 9412717W WO 9514007 B1 WO9514007 B1 WO 9514007B1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- groups
- compound
- formula
- hydrogen
- phenyl
- Prior art date
Links
- -1 Phenyl-alkyl imidazoles Chemical class 0.000 title claims 8
- 239000002464 receptor antagonist Substances 0.000 title 1
- 150000003839 salts Chemical class 0.000 claims abstract 18
- 239000011780 sodium chloride Substances 0.000 claims abstract 18
- 150000001875 compounds Chemical class 0.000 claims 24
- 125000004435 hydrogen atoms Chemical class [H]* 0.000 claims 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 10
- 125000000217 alkyl group Chemical group 0.000 claims 9
- 229910052739 hydrogen Inorganic materials 0.000 claims 9
- 239000001257 hydrogen Substances 0.000 claims 9
- 125000005843 halogen group Chemical group 0.000 claims 7
- 239000002253 acid Substances 0.000 claims 6
- 125000003545 alkoxy group Chemical group 0.000 claims 5
- 125000003118 aryl group Chemical group 0.000 claims 5
- 229910052736 halogen Inorganic materials 0.000 claims 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 208000008787 Cardiovascular Disease Diseases 0.000 claims 3
- 210000003169 Central Nervous System Anatomy 0.000 claims 3
- 125000001072 heteroaryl group Chemical group 0.000 claims 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- 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 2
- 206010020751 Hypersensitivity Diseases 0.000 claims 2
- 206010061218 Inflammation Diseases 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 125000000304 alkynyl group Chemical group 0.000 claims 2
- 201000005794 allergic hypersensitivity disease Diseases 0.000 claims 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 2
- 125000004432 carbon atoms Chemical group C* 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 125000002140 imidazol-4-yl group Chemical group [H]N1C([H])=NC([*])=C1[H] 0.000 claims 2
- 230000004054 inflammatory process Effects 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 150000002829 nitrogen Chemical group 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- JTNCEQNHURODLX-UHFFFAOYSA-N 2-phenylethanimidamide Chemical compound NC(=N)CC1=CC=CC=C1 JTNCEQNHURODLX-UHFFFAOYSA-N 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims 1
- PNKUSGQVOMIXLU-UHFFFAOYSA-N methanoic acid amidine Chemical compound NC=N PNKUSGQVOMIXLU-UHFFFAOYSA-N 0.000 claims 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
- 239000000546 pharmaceutic aid Substances 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract 2
- 200000000018 inflammatory disease Diseases 0.000 abstract 1
- 230000000144 pharmacologic effect Effects 0.000 abstract 1
Abstract
The invention provides novel phenyl-alkyl-imidazoles of formula (I) wherein A, R1, R2, m and n are as defined in the specification, and the group —(CH¿2?)n—A—R?1¿ is at the 3- or 4-position, together with their pharmaceutically acceptable salts. These phenyl-alkyl-imidazoles and salts have valuable pharmacological properties, especially CNS activities and activity against inflammatory disease.
Claims
AMENDED CLAIMS
[received by the International Bureau on 17 May 1995 (17.05.95);
original claims 1-23 amended; new claim 24 added (7 pages)]
A compound of the formula
wherein: A Is selected from -O-CO-NR1-, -O-CO-, -NR1-CO-NR1-, -NR1-CO-, -CO-NR1-, -CH2-NR1- and -C( NR1)-NR1-; the groups R1, which may be the same or different when there are two or three such groups in the molecule of formula I, are selected from hydrogen, and lower alkyl, aryl, cyctoalkyl, heterocydic and heterocyclyl-alkyl groups, and groups of the formula -(CH2)y-G. where G is selected from CO2R3, COR3, CONR3R4, OR3, SR3, NR3R4, heteroaryl and phenyl, which phenyl is optionally substituted by halogen, lower alkoxy or polyhalotoweralkyl, and y is an integer from 1 to 3;
R2 is selected from hydrogen and halogen atoms, and alkyl, alkenyl, alkynyl and trifluoromethyl groups, and groups of the formula OR3, SR3 and NR3R4; R3 and R4 are independently selected from hydrogen, and lower alkyl and cycloalkyl groups, or R3 and R4 together with the intervening nitrogen atom can form a saturated ring containing 4 to 6 carbon atoms that can be substituted with one or two lower alkyl groups;
with the proviso that, when y is 1 and G is OR3, SR3 or NR3R4, then neither R3 nor R4 is hydrogen; the group -(CH2)n-A-R1 is at the 4-position, and the group R2 is at any free position; m is an integer from 1 to 3;
and n is 0 or an integer from 1 to 3; or a pharmaceutically acceptable acid addition salt thereof;
or a pharmaceutically acceptable salt thereof with a base when G is CO2H; including a tautomeric form thereof.
2. A compound of the formula
wherein:
X is H2 or NH; the groups R1, which may be the same or different when there are two or three such groups in the molecuie of formula I, are selected from hydrogen, and lower alkyl, aryl, cycioalkyi, and heterocyclic groups, and groups of the formula
-(CH2)y-G, where G is selected from CO2R3, COR3, CONR3R4, OR3, SR3, NR3R4, heteroaryl and phenyl, which phenyl is optionally substituted by halogen, lower alkoxy or polyhaloioweralkyl, and y is an integer from 1 to 3; m, n, R3 and R4 are as defined in claim 1 ; the group -(CH2) n-CX-NR1R2 is at the 3- or 4-position; or a pharmaceutically acceptable acid addition salt thereof;
or a pharmaceutically acceptable salt thereof with a base when G is CO2H; including a tautomeric form thereof.
3. A compound as claimed in claim 2 wherein m is 1 or 2 and n is 0, 1 or 2.
4. A compound as claimed in claim 3 having the formula
wherein m, n, and R1 are as defined in claim 1.
5. A compound of the formula IB defined in claim 4 wherein the side chain -(CH2) n-C( =NH)NR1 2 is at the 4-position.
6. A compound as ciaimed in claim 5 wherein m is 1 or 2 and n is 0, 1 or 2.
7. A compound as claimed in claim 6 wherein the groups R1 , which may be the same or different, are selected from hydrogen, and aryl groups, and groups of the formula -(CH2)y-G, where G is selected from pyridyl and phenyl, which phenyl is optionally substituted by halogen, lower alkoxy or polyhaloioweralkyl, and y is 1 or 2.
8. A compound as claimed in claim 7 wherein one of the groups R1 is selected from hydrogen, 4-chlorophenylrnethyl, 4-methoxyphenylmethyl, 2-phenylethyl, 4-trifluoromβthylphenylmβthyl and 4-pyridylmethyl, and the other is a hydrogen atom.
9. A compound as claimed In claim 3 wherein A is -O-CO-NR1-,
10. A compound as claimed in claim 9 wherein the side chain
-(CH2)n-A-R1 is at the 4-position, m is 1 or 2 and n is 0, 1 or 2.
11. A compound as ciaimed in claim 10 wherein the groups R1 , which may be the same or different, are selected from hydrogen, and aryl groups, and groups of the formula -(CH2)y-G, where G is selected from pyridyl and phenyl, which phenyl is optionally substituted by halogen, lower alkoxy or polyhaloioweralkyi, and y is 1 or 2.
12. A compound as ciaimed in claim 11 wherein one of the groups R1 is selected from hydrogen, 4-chlorophenylmethyl, 4-mβthoxyphenylmethyl,
2-phenylethyl, 4-trifluoromethylphenylmethyl and 4-pyridylmethyl, and the other is a hydrogen atom.
13. A compound as claimed in claim 1 having the formula
14. A compound of claim 1 , having the name N-[(4-chlorophenyl)methyl}-4-[(1H-imidazol-4-yl)methyl)benzene methanimidamide and the structure:
or a pharmaceutically acceptable acid addition salt thereof. 15. A compound of claim 1 , having the name N-[(4-chtorophenyl)methyl]-4-{(1H-imidazol-4-yl)methyl]benzene ethanimidamide and the structure:
or a pharmaceutically acceptable acid addition salt thereof. 16. The dihydrochloride of the compound of claim 14. 17. The dihydrochloride of the compound of claim 15.
16. A pharmaceutical composition containing as active ingredient a
compound of the formula I defined in claim 1 or of the formula IC defined in claim 2 or a pharmaceutically acceptable acid addition salt thereof or a pharmaceutically acceptable salt thereof with a base when G is CO2H, together with a pharmaceutical carrier or excipient.
19. A method for treating inflammation, which comprises administering to a patient suffering from inflammation an effective amount of a compound or salt as claimed in claim 1 or claim 2.
20. A method for treating allergy, which comprises administering to a patient suffering from allergy an effective amount of a compound or salt as claimed in claim 1 or claim 2.
21. A method for treating diseases of the Gl-tract, which comprises
administering to a patient suffering from a disease of the Gl-tract an effective amount of a compound or salt as claimed in claim 1 or claim 2. 22. A method for treading cardiovascular disease, which comprises
administering to a patient suffering from cardiovascular disease an effective amount of a compound or salt as ciaimed in claim 1 or claim 2.
23. A method for treating disturbances of the central nervous system, which comprises administering to a patient suffering from disturbances of the central nervous system an effective amount of a compound or salt of the formula
wherein:
A is selected from -O-CO-NR1-, -O-CO-, -NR1-CO-NR1-, -NR1-CO-.
-CO-NR1-, -COO-, -CH2-NR1- and -C(:NR1)-NR1-; the groups R1 , which may be the same or different when there are two or three such groups in the molecule of formula I, are selected from hydrogen, and lower alkyl, aryl, cycloalkyt, heterocyclic and hθterocyclyl-alky! groups, and groups of the formula -(CH2)y-G, where G is selected from CO2R3, COR3, CONR3R4, OR3,
SR3, NR3R4, heteroaryl and phenyl, which phenyl is optionally substituted by halogen, lower alkoxy or polyhaloioweralkyl, and y is an integer from 1 to 3;
R2 is selected from hydrogen and halogen atoms, and alkyl, alkenyl, alkynyl and trifluoromethyl groups, and groups of the formula OR3, SR3 and NR3R4; R3 and R4 are independently selected from hydrogen, and lower alkyl and cydoalkyl groups, or R3 and R4 together with the intervening nitrogen atom can form a saturated ring containing 4 to 6 carbon atoms that can be substituted with one or two lower alkyl groups;
with the proviso that, when y is 1 and G is OR3, SR3 or NRSR4, then neither R3 nor R4 is hydrogen; the group -(CH2)n- A-R1 is at the 4-position, and the group R2 is at any free position; m is an integer from 1 to 3;
and n is 0 or an integer from 1 to 3; or a pharmaceutically acceptable acid addition salt thereof;
or a pharmaceutically acceptable salt thereof with a base when G is CO2H; including a tautomeric form thereof.
24. A method for treating disturbances of the central nervous system, which comprises administering to a patient suffering from cardiovascular disease an effective amount of a compound or salt as claimed in claim 2.
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT95902442T ATE234290T1 (en) | 1993-11-15 | 1994-11-10 | PHENYLALKYL-IMIDAZOLE AS H3 RECEPTOR ANTAGONISTS |
| DE69432263T DE69432263T2 (en) | 1993-11-15 | 1994-11-10 | PHENYLALKYL IMIDAZOLES AS H3 RECEPTOR ANTAGONISTS |
| AU11712/95A AU693142B2 (en) | 1993-11-15 | 1994-11-10 | Phenyl-alkyl imidazoles as H3-receptor antagonists |
| EP95902442A EP0729459B1 (en) | 1993-11-15 | 1994-11-10 | Phenyl-alkyl imidazoles as h3-receptor antagonists |
| CA002176557A CA2176557C (en) | 1993-11-15 | 1994-11-10 | Phenyl-alkyl imidazoles as h3-receptor antagonists |
| NZ276883A NZ276883A (en) | 1993-11-15 | 1994-11-10 | 1h-imidazol-4-yl)alkyl]benzene derivatives |
| JP7514478A JPH09505298A (en) | 1993-11-15 | 1994-11-10 | Phenyl-alkyl imidazoles as H-lower 3-receptor antagonists |
| US08/469,941 US5578616A (en) | 1993-11-15 | 1995-06-06 | Phenyl-alkyl-imidazoles |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US15323193A | 1993-11-15 | 1993-11-15 | |
| US08/153,231 | 1993-11-15 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| WO1995014007A1 WO1995014007A1 (en) | 1995-05-26 |
| WO1995014007B1 true WO1995014007B1 (en) | 1995-06-15 |
Family
ID=22546320
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/US1994/012717 WO1995014007A1 (en) | 1993-11-15 | 1994-11-10 | Phenyl-alkyl imidazoles as h3-receptor antagonists |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US5578616A (en) |
| EP (1) | EP0729459B1 (en) |
| JP (1) | JPH09505298A (en) |
| AT (1) | ATE234290T1 (en) |
| AU (1) | AU693142B2 (en) |
| DE (1) | DE69432263T2 (en) |
| ES (1) | ES2188649T3 (en) |
| HU (1) | HUT74386A (en) |
| NZ (2) | NZ330898A (en) |
| WO (1) | WO1995014007A1 (en) |
Families Citing this family (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19615262A1 (en) * | 1996-04-18 | 1997-10-23 | Bayer Ag | Hetero-linked phenylglycinolamides |
| SG72827A1 (en) * | 1997-06-23 | 2000-05-23 | Hoffmann La Roche | Phenyl-and aminophenyl-alkylsulfonamide and urea derivatives |
| GB2344588B (en) * | 1997-07-25 | 2001-11-14 | Black James Foundation | 1H-4(5)-substituted imidazole derivatives their preparation and their use as histamine H 3 receptor ligands |
| GB9715814D0 (en) * | 1997-07-25 | 1997-10-01 | Black James Foundation | Histamine H3 receptor ligands |
| US6407132B1 (en) * | 1997-07-25 | 2002-06-18 | James Black Foundation Limited | Substituted imidazole derivatives and their use as histamine H3 receptor ligands |
| US5990147A (en) * | 1997-11-07 | 1999-11-23 | Schering Corporation | H3 receptor ligands of the phenyl-alkyl-imidazoles type |
| US6034251A (en) * | 1997-11-07 | 2000-03-07 | Schering Corporation | Phenyl-alkyl-imidazoles |
| CA2309121A1 (en) * | 1997-11-07 | 1999-05-20 | Schering Corporation | Phenyl-alkyl-imidazoles as h3 receptor antagonists |
| ES2174510T3 (en) * | 1997-11-07 | 2002-11-01 | Schering Corp | LEGANDS OF THE H3 RECEPTOR OF THE FENIL-ALQUIL-IMIDAZOL TYPE. |
| US6503935B1 (en) | 1998-08-07 | 2003-01-07 | Abbott Laboratories | Imidazoles and related compounds as α1A agonists |
| US6133291A (en) * | 1998-10-16 | 2000-10-17 | Schering Corporation | N-(imidazolylalkyl)substituted cyclic amines as histamine-H3 agonists or antagonists |
| US6100279A (en) * | 1998-11-05 | 2000-08-08 | Schering Corporation | Imidazoylalkyl substituted with a five, six or seven membered heterocyclic ring containing one nitrogen atom |
| WO2000042023A1 (en) | 1999-01-18 | 2000-07-20 | Novo Nordisk A/S | Substituted imidazoles, their preparation and use |
| US6211182B1 (en) | 1999-03-08 | 2001-04-03 | Schering Corporation | Imidazole compounds substituted with a six or seven membered heterocyclic ring containing two nitrogen atoms |
| US6908926B1 (en) | 1999-04-16 | 2005-06-21 | Novo Nordisk A/S | Substituted imidazoles, their preparation and use |
| US6437147B1 (en) | 2000-03-17 | 2002-08-20 | Novo Nordisk | Imidazole compounds |
| US6610721B2 (en) | 2000-03-17 | 2003-08-26 | Novo Nordisk A/S | Imidazo heterocyclic compounds |
| CA2419027A1 (en) | 2000-08-08 | 2002-02-14 | Ortho-Mcneil Pharmaceutical, Inc. | Bicyclic compounds as h3 receptor ligands |
| MXPA03001267A (en) | 2000-08-08 | 2004-07-30 | Johnson & Johnson | Non-imidazole aryloxyalkylamines. |
| CA2419036A1 (en) | 2000-08-08 | 2002-02-14 | Ortho-Mcneil Pharmaceutical, Inc. | Non-imidazole aryloxypiperidines as h3 receptor ligands |
| AR031612A1 (en) | 2000-09-20 | 2003-09-24 | Schering Corp | REPLACED IMIDAZOLS, PHARMACEUTICAL COMPOSITIONS, METHOD FOR THEIR PREPARATION AND THE USE OF THEM TO PREPARE A MEDICINAL PRODUCT AS AGONISTS OR ANTAGONISTS H1 AND H3 OF HISTAMINE |
| CN1461299A (en) | 2000-09-20 | 2003-12-10 | 先灵公司 | Substituted imidazoles as dual histamine H1 and H3 agonists or antagonists |
| AU2002241459A1 (en) | 2000-09-20 | 2002-06-11 | Schering Corporation | Substituted imidazoles as dual histamine h1 and h3 agonists or antagonists |
| AU2001292730A1 (en) | 2000-09-20 | 2002-04-02 | Schering Corporation | Substituted imidazoles as dual histamine h1 and h3 agonists or antgonists |
| PE20020507A1 (en) | 2000-10-17 | 2002-06-25 | Schering Corp | NON-IMIDAZOLE COMPOUNDS AS ANTAGONISTS OF THE HISTAMINE H3 RECEPTOR |
| WO2002067938A2 (en) * | 2000-10-30 | 2002-09-06 | Schering Corporation | Treating or reducing the risk of cardiovascular disease |
| WO2002072093A2 (en) | 2001-02-08 | 2002-09-19 | Schering Corporation | Use of dual h3/m2 antagonists with a bipiperidinic structure in the treatment of cognition deficit disorders |
| CA2440559C (en) | 2001-03-13 | 2010-09-21 | Schering Corporation | Novel non-imidazole compounds |
| US7880017B2 (en) * | 2003-11-11 | 2011-02-01 | Allergan, Inc. | Process for the synthesis of imidazoles |
| US7183305B2 (en) * | 2003-11-11 | 2007-02-27 | Allergan, Inc. | Process for the synthesis of imidazoles |
| EP1707203A1 (en) | 2005-04-01 | 2006-10-04 | Bioprojet | Treatment of parkinson's disease obstructive sleep apnea, dementia with lewy bodies, vascular dementia with non-imidazole alkylamines histamine H3- receptor ligands |
| EP1717235A3 (en) | 2005-04-29 | 2007-02-28 | Bioprojet | Phenoxypropylpiperidines and -pyrrolidines and their use as histamine H3-receptor ligands |
| EP1717233A1 (en) * | 2005-04-29 | 2006-11-02 | Bioprojet | Histamine H3-receptor ligands and their therapeutic application |
| US7332604B2 (en) | 2005-09-20 | 2008-02-19 | Schering Corporation | 1-[[1-[(2-Amino-6-methyl-4-pyridinyl)methyl]-4-fluoro-4-piperidinyl]carbonyl]-4-[2-(2-pyridinyl)-3H-imidazo[4,5-b]pyridin-3-yl]piperidine |
| US20080146523A1 (en) | 2006-12-18 | 2008-06-19 | Guido Galley | Imidazole derivatives |
| US8492422B2 (en) * | 2010-09-16 | 2013-07-23 | Allergan, Inc. | Ester pro-drugs of [3-(1-(1H-imidazol-4-yl)ethyl)-2-methylphenyl] methanol for treating skin diseases and conditions |
| WO2013078151A1 (en) | 2011-11-21 | 2013-05-30 | Allergan, Inc. | Pharmaceutical compositions comprising 4-[1-(2,3-dimethylphenyl)ethyl]-3h-imidazole derivatives for treating retinal diseases |
| CN104602690A (en) * | 2012-08-29 | 2015-05-06 | 默克专利股份有限公司 | DDR2 inhibitors for the treatment of osteoarthritis |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU518569B2 (en) * | 1979-08-07 | 1981-10-08 | Farmos-Yhtyma Oy | 4-benzyl- and 4-benzoyl imidazole derivatives |
| GB8626287D0 (en) * | 1986-11-04 | 1986-12-03 | Ucb Sa | Substituted 1h-imidazoles |
| JPH01242571A (en) * | 1988-03-22 | 1989-09-27 | Mitsui Petrochem Ind Ltd | Production of imidazole derivative |
| GB8810067D0 (en) * | 1988-04-28 | 1988-06-02 | Ucb Sa | Substituted 1-(1h-imidazol-4-yl)alkyl-benzamides |
| GB8916947D0 (en) * | 1989-07-25 | 1989-09-13 | Smith Kline French Lab | Medicaments |
| GB9115740D0 (en) * | 1991-07-20 | 1991-09-04 | Smithkline Beecham Plc | Medicaments |
| FR2686084B1 (en) * | 1992-01-10 | 1995-12-22 | Bioprojet Soc Civ | NEW IMIDAZOLE DERIVATIVES, THEIR PREPARATION AND THEIR THERAPEUTIC APPLICATIONS. |
-
1994
- 1994-11-10 AT AT95902442T patent/ATE234290T1/en not_active IP Right Cessation
- 1994-11-10 AU AU11712/95A patent/AU693142B2/en not_active Ceased
- 1994-11-10 HU HU9601282A patent/HUT74386A/en unknown
- 1994-11-10 DE DE69432263T patent/DE69432263T2/en not_active Expired - Fee Related
- 1994-11-10 ES ES95902442T patent/ES2188649T3/en not_active Expired - Lifetime
- 1994-11-10 WO PCT/US1994/012717 patent/WO1995014007A1/en active IP Right Grant
- 1994-11-10 JP JP7514478A patent/JPH09505298A/en not_active Withdrawn
- 1994-11-10 NZ NZ330898A patent/NZ330898A/en unknown
- 1994-11-10 EP EP95902442A patent/EP0729459B1/en not_active Expired - Lifetime
- 1994-11-10 NZ NZ276883A patent/NZ276883A/en unknown
-
1995
- 1995-06-06 US US08/469,941 patent/US5578616A/en not_active Expired - Lifetime
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