WO1998015535B1 - 1,4-benzodiazepinones and their uses as cck antagonists - Google Patents
1,4-benzodiazepinones and their uses as cck antagonistsInfo
- Publication number
- WO1998015535B1 WO1998015535B1 PCT/JP1997/003483 JP9703483W WO9815535B1 WO 1998015535 B1 WO1998015535 B1 WO 1998015535B1 JP 9703483 W JP9703483 W JP 9703483W WO 9815535 B1 WO9815535 B1 WO 9815535B1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- compound
- formula
- cycloalkyl
- benzodiazepinones
- pharmaceutically acceptable
- Prior art date
Links
- 239000005557 antagonist Substances 0.000 title abstract 2
- RGGLEJFUEMKQSH-UHFFFAOYSA-N 1,4-benzodiazepin-2-one Chemical class O=C1C=NC=C2C=CC=CC2=N1 RGGLEJFUEMKQSH-UHFFFAOYSA-N 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims abstract 4
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 2
- 239000001257 hydrogen Substances 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims 5
- -1 N,N-dimethylamino Chemical group 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 125000005037 alkyl phenyl group Chemical group 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 238000010276 construction Methods 0.000 claims 1
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 102100025841 Cholecystokinin Human genes 0.000 abstract 1
- 101800001982 Cholecystokinin Proteins 0.000 abstract 1
- 229940053197 benzodiazepine derivative antiepileptics Drugs 0.000 abstract 1
- 125000003310 benzodiazepinyl group Chemical class N1N=C(C=CC2=C1C=CC=C2)* 0.000 abstract 1
- 229940107137 cholecystokinin Drugs 0.000 abstract 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 abstract 1
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical group 0.000 abstract 1
- 150000002431 hydrogen Chemical group 0.000 abstract 1
- IZTQOLKUZKXIRV-YRVFCXMDSA-N sincalide Chemical compound C([C@@H](C(=O)N[C@@H](CCSC)C(=O)NCC(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(N)=O)NC(=O)[C@@H](N)CC(O)=O)C1=CC=C(OS(O)(=O)=O)C=C1 IZTQOLKUZKXIRV-YRVFCXMDSA-N 0.000 abstract 1
Abstract
Benzodiazepine derivatives of formula (I) wherein R2 is alkyl or cycloalkyl-alkyl when R4 is hydrogen, or R2 is a variety of specified groups when R4 is alkyl, halogen or dialkylamino, are useful as cholecystokinin antagonists.
Claims
[received by the International Bureau on 23 April 1998 (23.04.98); original claim 5 amended; remaining claims unchanged (1 page)]
(3) chlorine, or
(4) N,N-dimethylamino, with proviso that when R4 is hydrogen, then R- is isopropyl, isobutyl, methyl, isopenty], ethyl, butyl or cyclohexylmethyl,
or a pharmaceutically acceptable salt thereof.
5. A compound of claim 1, which is a compound of the formula:
wherein R: is lower alkyl or C3-C3 cycloalkyl,
R4 is lower alkyl,
R5 is C3-C3 cycloalkyl,
R6 is lower alkylphenyl and
A is lower alkylene,
or a pharmaceutically acceptable salt thereof.
6. A compound of claim 1, which is a compound of the formula:
326
STATEMENT UNDER ARTICLE 19
The formula in claim 5 is corrected by changing the broken line between a carbon of benzene ring and R4 into a solid line, so that the construction of the compound is clarified.
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP97941281A EP0934282A1 (en) | 1996-10-08 | 1997-09-29 | 1,4-benzodiazepinones and their uses as cck antagonists |
| US09/269,752 US6291452B1 (en) | 1996-10-08 | 1997-09-29 | 1,4-benzodiazepinones and their uses as CCK antagonists |
| JP51737298A JP2001504454A (en) | 1996-10-08 | 1997-09-29 | Benzodiazepine derivatives |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AUPO2843 | 1996-10-08 | ||
| AUPO2843A AUPO284396A0 (en) | 1996-10-08 | 1996-10-08 | Benzodiazepine derivatives |
Related Child Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US09/269,752 A-371-Of-International US6291452B1 (en) | 1996-10-08 | 1997-09-29 | 1,4-benzodiazepinones and their uses as CCK antagonists |
| US09/897,888 Continuation US20020002163A1 (en) | 1996-10-08 | 2001-07-05 | 1,4-benzodiazepinones and their uses as CCK antagonists |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| WO1998015535A1 WO1998015535A1 (en) | 1998-04-16 |
| WO1998015535B1 true WO1998015535B1 (en) | 1998-06-11 |
Family
ID=3797154
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/JP1997/003483 WO1998015535A1 (en) | 1996-10-08 | 1997-09-29 | 1,4-benzodiazepinones and their uses as cck antagonists |
Country Status (5)
| Country | Link |
|---|---|
| US (3) | US6291452B1 (en) |
| EP (1) | EP0934282A1 (en) |
| JP (1) | JP2001504454A (en) |
| AU (1) | AUPO284396A0 (en) |
| WO (1) | WO1998015535A1 (en) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6825160B1 (en) | 1999-08-27 | 2004-11-30 | Procter & Gamble Company | Color safe laundry methods employing cationic formulation components |
| DE60028387T2 (en) * | 1999-08-27 | 2007-05-24 | The Procter & Gamble Company, Cincinnati | BLEACHING COMPOUNDS, COMPOSITIONS AND WASHING PROCESSES |
| US6818607B1 (en) | 1999-08-27 | 2004-11-16 | Procter & Gamble Company | Bleach boosting components, compositions and laundry methods |
| MXPA02002124A (en) | 1999-08-27 | 2002-09-18 | Procter & Gamble | Stability enhancing formulation components, compositions and laundry methods employing same. |
| US7109156B1 (en) | 1999-08-27 | 2006-09-19 | Procter & Gamble Company | Controlled availability of formulation components, compositions and laundry methods employing same |
| US6903060B1 (en) | 1999-08-27 | 2005-06-07 | Procter & Gamble Company | Stable formulation components, compositions and laundry methods employing same |
| US6821935B1 (en) | 1999-08-27 | 2004-11-23 | Procter & Gamble Company | Color safe laundry methods employing zwitterionic formulation components |
| US7557076B2 (en) | 2002-06-06 | 2009-07-07 | The Procter & Gamble Company | Organic catalyst with enhanced enzyme compatibility |
| US7169744B2 (en) | 2002-06-06 | 2007-01-30 | Procter & Gamble Company | Organic catalyst with enhanced solubility |
| JP4705908B2 (en) * | 2003-04-15 | 2011-06-22 | メルク・シャープ・エンド・ドーム・コーポレイション | CGRP receptor antagonist |
| EP1641781B1 (en) * | 2003-06-26 | 2013-03-06 | Merck Sharp & Dohme Corp. | Benzodiazepine CGRP receptor antagonists |
| CA2529196A1 (en) * | 2003-06-26 | 2005-02-17 | Merck & Co., Inc. | Benzodiazepine cgrp receptor antagonists |
| AU2004285636A1 (en) * | 2003-10-23 | 2005-05-12 | Bayer Cropscience Aktiengesellschaft | Isopentyl carboxanilides for combating undesired micro-organisms |
| DE10352067A1 (en) * | 2003-10-23 | 2005-05-25 | Bayer Cropscience Ag | Isopentylcarboxanilide |
| CA2554351A1 (en) * | 2004-01-29 | 2005-08-11 | Merck & Co., Inc. | Cgrp receptor antagonists |
| AR051659A1 (en) | 2005-06-17 | 2007-01-31 | Procter & Gamble | A COMPOSITION THAT INCLUDES AN ORGANIC CATALYST WITH IMPROVED ENZYMATIC COMPATIBILITY |
| GB201414116D0 (en) | 2014-08-08 | 2014-09-24 | Trio Medicines Ltd | Benzodiazepine derivatives |
| GB201513979D0 (en) | 2015-08-07 | 2015-09-23 | Trio Medicines Ltd | Synthesis of benzodiazepine derivatives |
| CN113816914B (en) * | 2021-09-28 | 2024-04-09 | 华中药业股份有限公司 | Preparation method of lorazepam intermediate |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4820834A (en) * | 1984-06-26 | 1989-04-11 | Merck & Co., Inc. | Benzodiazepine analogs |
| US4970207A (en) | 1988-07-07 | 1990-11-13 | Fujisawa Pharmaceutical Company, Ltd. | Benzodiazepine derivatives |
| US5264433A (en) | 1988-07-07 | 1993-11-23 | Fujisawa Pharmaceutical Co., Ltd. | Benzodiazepine derivatives |
| IL91361A (en) | 1988-09-09 | 1994-10-07 | Fujisawa Pharmaceutical Co | Disubstituted 1,9-annelated [1,4] benzodiazepinone compounds, processes for the preparation thereof and pharmaceutical compositions containing the same |
| US5248679A (en) | 1988-09-09 | 1993-09-28 | Fujisawa Pharmaceutical Co., Ltd. | Tricyclic compounds |
| IL96613A0 (en) * | 1989-12-18 | 1991-09-16 | Merck & Co Inc | Pharmaceutical compositions containing benzodiazepine analogs |
| GB9018601D0 (en) | 1990-08-24 | 1990-10-10 | Fujisawa Pharmaceutical Co | Tricyclic compounds |
| CA2068355A1 (en) * | 1991-05-14 | 1992-11-15 | Mark S. Chambers | Benzodiazephine derivatives, compositions containing them and their use in therapy |
| EP0549039B1 (en) * | 1991-12-20 | 1995-08-09 | MERCK SHARP & DOHME LTD. | 3-Phenylureido-1,4-Benzodiazepinones and their use as cholecystokinin or gastrin antagonists |
| GB9203790D0 (en) * | 1992-02-21 | 1992-04-08 | Merck Sharp & Dohme | Therapeutic agents |
| IL104853A (en) * | 1992-02-27 | 1997-11-20 | Yamanouchi Pharma Co Ltd | Benzodiazepine derivatives, their preparation and pharmaceutical compositions containing them |
| AU670939B2 (en) * | 1992-03-16 | 1996-08-08 | Merck Sharp & Dohme Limited | Benzodiazepine derivatives, compositions containing them and their use in therapy |
| AU670431B2 (en) * | 1992-03-24 | 1996-07-18 | Merck Sharp & Dohme Limited | 3-ureido substituted benzodiazepin-2-ones having cholecystokinin and/or gastrin antagonistic activity and their use in therapy |
| US5360802A (en) * | 1992-05-11 | 1994-11-01 | Merck Sharpe & Dohme Ltd. | Benzodiazepine derivatives, compositions containing them and their use in therapy |
| GB9225492D0 (en) * | 1992-12-05 | 1993-01-27 | Glaxo Group Ltd | Amine derivatives |
| JPH09511998A (en) * | 1994-04-15 | 1997-12-02 | グラクソ、ウェルカム、インコーポレーテッド | Method for inducing cholecystokinin agonist activity using 1,4-benzodiazepine compound |
| EP0804425A2 (en) | 1994-07-29 | 1997-11-05 | Fujisawa Pharmaceutical Co., Ltd. | Benzodiazepine derivatives |
| US5556969A (en) * | 1994-12-07 | 1996-09-17 | Merck Sharp & Dohme Ltd. | Benzodiazepine derivatives |
| US5929071A (en) * | 1996-07-02 | 1999-07-27 | Merck & Co., Inc. | Method for the treatment of preterm labor |
-
1996
- 1996-10-08 AU AUPO2843A patent/AUPO284396A0/en not_active Abandoned
-
1997
- 1997-09-29 US US09/269,752 patent/US6291452B1/en not_active Expired - Fee Related
- 1997-09-29 JP JP51737298A patent/JP2001504454A/en active Pending
- 1997-09-29 EP EP97941281A patent/EP0934282A1/en not_active Withdrawn
- 1997-09-29 WO PCT/JP1997/003483 patent/WO1998015535A1/en not_active Application Discontinuation
-
2001
- 2001-07-05 US US09/897,888 patent/US20020002163A1/en not_active Abandoned
-
2002
- 2002-03-20 US US10/101,297 patent/US20020183313A1/en not_active Abandoned
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