CA2108486A1 - Crystalline(r)-(-)-2-cycloheptyl-n-methylsulfonyl- [4-(2-quinolinyl-methoxy)-phenyl]-acetamide - Google Patents
Crystalline(r)-(-)-2-cycloheptyl-n-methylsulfonyl- [4-(2-quinolinyl-methoxy)-phenyl]-acetamideInfo
- Publication number
- CA2108486A1 CA2108486A1 CA002108486A CA2108486A CA2108486A1 CA 2108486 A1 CA2108486 A1 CA 2108486A1 CA 002108486 A CA002108486 A CA 002108486A CA 2108486 A CA2108486 A CA 2108486A CA 2108486 A1 CA2108486 A1 CA 2108486A1
- Authority
- CA
- Canada
- Prior art keywords
- crystalline
- water
- process according
- active compound
- solvent
- Prior art date
- Legal status (The legal status 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 status listed.)
- Abandoned
Links
- 150000001875 compounds Chemical class 0.000 claims abstract description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 22
- 239000003814 drug Substances 0.000 claims abstract description 13
- 230000004048 modification Effects 0.000 claims abstract description 13
- 238000012986 modification Methods 0.000 claims abstract description 13
- YAWBFCPZMALJCE-RUZDIDTESA-N (2r)-2-cycloheptyl-n-methylsulfonyl-2-[4-(quinolin-2-ylmethoxy)phenyl]acetamide Chemical compound C1([C@@H](C(=O)NS(=O)(=O)C)C=2C=CC(OCC=3N=C4C=CC=CC4=CC=3)=CC=2)CCCCCC1 YAWBFCPZMALJCE-RUZDIDTESA-N 0.000 claims abstract description 5
- 239000003960 organic solvent Substances 0.000 claims abstract description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 16
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 8
- 239000013078 crystal Substances 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 239000007787 solid Substances 0.000 claims description 5
- 150000001298 alcohols Chemical class 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 239000003085 diluting agent Substances 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 claims 1
- 238000003756 stirring Methods 0.000 abstract description 3
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 239000003112 inhibitor Substances 0.000 abstract description 2
- 150000002617 leukotrienes Chemical class 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- 238000002360 preparation method Methods 0.000 description 12
- 239000000725 suspension Substances 0.000 description 5
- 239000000825 pharmaceutical preparation Substances 0.000 description 3
- 239000011877 solvent mixture Substances 0.000 description 3
- 238000001757 thermogravimetry curve Methods 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- -1 for example Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D215/14—Radicals substituted by oxygen atoms
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Quinoline Compounds (AREA)
Abstract
A b s t r a c t (R)-(-)-2-cycloheptyl-N-methylsulfonyl- [4-(2-quinolinyl-methoxy)-phenyl]-acetamide, which is an inhibitor of leukotriene synthesis, is prepared in crystalline form by suspending the active compound in non-crystalline form in inert organic solvents, optionally in the presence of water, and, at elevated temperature, converting it by stirring into the crystalline modification. The crystal-line active compound is suitable, in particular, for preparing medicaments having increased storage stability and temperature resistance.
Description
21(38~86 The invention relates to a crystalline form of the (R)-(-)-2-cycloheptyl-N-methylsulfonyl- [4-(2-quinol inyl -methoxy)-phenyl]-acetamide, a process for its preparation and its use in medicaments.
(R)-(-)-2-Cycloheptyl-N-methylsulfo n y 1 - t 4-(2-qui no 1 i ny 1 -methoxy)-phenyl]-acetamide of the formula (I), ~ N ~
o,~o which is an inhibitor of leukotriene synthesis, its preparation and its use in medicaments, is already described in EP 344 519.
According to the preparation process described therein, the compound of the formula (I) is obtained in the form of a non-crystalline powder. A solvate-free, crystalline modification is hitherto unknown.
However, it has become evident that the non-crystalline form of the compound (I) has crucial disadvantages, in particular in the preparation of solid medicaments. Thus, medicaments which contain the compound of the formula (I) Le A 29 305 - 1 -2108~86 in the dmorphous form exhibit very unsatisfactory storage stability for example Thi s phy5 i cal instability which preferentially arises when the preparations are stored over a relatively long period of time at tempera-tures above 30C, impairs the absorption efficacy and, inparticular, the safety of these preparations. It is therefore of qreat importance to make available a stable form of the compound of the formula (I), which does not possess the abovementioned disadvantages, for preparing medicaments.
A novel crystalline form of the compound (R)-(-)-2-cyclo-heptyl-N-methylsulfonyl- [4-(2-quinolinylmethoxy)-phenyl]-acetamide has now been found which is distin-guished, in comparison with the known non-crystalline form, by increased physical stability and reduced sensi-tivity to pressure, and is therefore considerably more suitable for the preparation of various medicament forms than is the non-crystalline form.
The preparation of the novel crystalline form of the compound of the formula (I) according to the invention is effected, e.g., by the compound of the formula (I) in non-crystalline form being suspended in inert organic solvents, optionally in the presence of water, and being treated at elevated temperatures until it is quantita-tively converted into the crystalline modification, andthe resulting crystals of the crystalline modification then being separated off by customary methods and, to remove any solvent residues which may be present, dried Le A 29 305 - 2 -210848~
to constant weight at temperatures of +20C to +70C.
The duration of the conversion depends on the nature of the solvent and the temperature selected. As a rule, it amounts to several days to weeks.
Lower alcohols having 1 to 6 carbon atoms are preferably employed as solvents; ethanol or isopropanol is pre-ferably used. In this context, mixtures of the alcohols with water in the ratio of one part of alcohol to 20 parts of water, preferably of one part of alcohol to 10 parts of water, are very particularly preferred. The use of ethanol or isopropanolJwater mixtures in the ratio 1:8 is very particularly preferred.
The conversion of the non-crystalline form into the crystalline form of the compound of the formula (I) is usually effected by stirring or shaking the suspension at elevated temperatures.
The separation of the crystals from the water/solvent mixture takes place according to customary methods, such as, for example, by filtration, decanting off, centri-fugation or the like. Subsequently, the crystals aredried to constant mass at an elevated temperature, for example at +50C or in vacuo.
The complete conversion of the non-crystalline form into the crystalline modification is determined by DSC (dif-ferential scanning calorimetry), spectroscopic or Le A 29 305 - 3 -- 2~0~86 crystallographic methods.
A more rapid process, which is particularly suitable for preparing relatively large quantities of crystalline active compound, is achieved with the aid of seed crys-tals, by, for example, the non-crystalline active com-pound being suspended in a mixture of water and ethanol in the ratio 8:1, the suspension being heated to +70C, some seeds of the crystalline active compound being added, and the mixture being stirred for about 4 h until the non-crystalline active compound has been quantita tively converted into the crystalline active compound.
However~ if the time of stirring is extended, the com-plete conversion can also be effected at an elevated temperature below +70C, for example in a temperature range of ~40~ to +60C, or in other solvent mixtures, such as, for example, water and isopropanol, or in solvent mixtures with other mixture ratios, such as, for example, in mixtures of water and alcohol in the ratio of 15:1 to 25:1.
The crystalline modification of the (R)-(-)-2-cyclo-heptyl-N-methylsulfony1- [4-(2-quinolinylmethoxy)-phenyl]-acetamide according to the invention possesses a characteristic IR spectrum.
The thermogram of the crystalline modification according to the invention, recorded by means of DSC (differential scanning calorLmetry) under atmospheric pressure, shows an endothermic melting peak at 124-127C and thus differs Le A 29 305 - 4 -2108~6 unan~iguously from the thermograms of other forms of the active compound.
soth the X-ray diffractograms and the 13C solid NMR
spectra are characteristic of the crystalline modifica-tion according to the invention. The density of the crystalline (R)-(~)-2-cycloheptyl-N-methylsulfonyl- t4-(2-quino 1 inyl methoxy)-phenyl]-acetamide is 1.30 g/cm3.
The present invention also includes pharmaceutical preparations which, besides inert non-toxic pharmaceuti-cally suitable auxiliaries and vehicles, contain thecrystalline form of the compound of the formula (I) according to the invention, or which comprise the crys-talline modification of the compound of the formula (I), as well as processes for producing these preparations. In this context, solid drug forms and suspensions are to be mentioned as being preferred. The crystalline active compound is particularly suitable for preparing solid medicament~, e.g. in the form of tablets, pill8, coated tablets or capsules.
In these preparations, the novel crystalline modification of the compound of the formula (I) should be present in a concentration of 0.1 to 99.5~ by weight, preferably of 0.5 to 95~ by weight, of the total mixture.
As well as the crystalline modification of the compound of the formula (I), the pharmaceutical preparations may also contain other pharmaceutical active compounds.
Le A 29 305 - 5 _ 21~84~6 The abovementioned pharmaceutical preparations can be prepared in a customary manner by known methods, for example with one or more auxiliaries or vehicles.
Preparation examples Example 1 Preparation of seed crystals 1 g of non-crystalline active compound is suspended in a water/isopropanol mixture (8 ml:1 ml), and stirred at +50C for 14 days. The suspension is subsequently fil-tered and dried in vacuo to constant mass.
Example 2 Crystallisation by seeding 1 g of non-crystalline active compound is suspended in a water/ethanol mixture (8 ml:l ml), seeded with a few seed crystals and stirred at +70C for 4 hours. The suspension is subsequently filtered and dried to constant mass.
Le A 29 305 - 6 -
(R)-(-)-2-Cycloheptyl-N-methylsulfo n y 1 - t 4-(2-qui no 1 i ny 1 -methoxy)-phenyl]-acetamide of the formula (I), ~ N ~
o,~o which is an inhibitor of leukotriene synthesis, its preparation and its use in medicaments, is already described in EP 344 519.
According to the preparation process described therein, the compound of the formula (I) is obtained in the form of a non-crystalline powder. A solvate-free, crystalline modification is hitherto unknown.
However, it has become evident that the non-crystalline form of the compound (I) has crucial disadvantages, in particular in the preparation of solid medicaments. Thus, medicaments which contain the compound of the formula (I) Le A 29 305 - 1 -2108~86 in the dmorphous form exhibit very unsatisfactory storage stability for example Thi s phy5 i cal instability which preferentially arises when the preparations are stored over a relatively long period of time at tempera-tures above 30C, impairs the absorption efficacy and, inparticular, the safety of these preparations. It is therefore of qreat importance to make available a stable form of the compound of the formula (I), which does not possess the abovementioned disadvantages, for preparing medicaments.
A novel crystalline form of the compound (R)-(-)-2-cyclo-heptyl-N-methylsulfonyl- [4-(2-quinolinylmethoxy)-phenyl]-acetamide has now been found which is distin-guished, in comparison with the known non-crystalline form, by increased physical stability and reduced sensi-tivity to pressure, and is therefore considerably more suitable for the preparation of various medicament forms than is the non-crystalline form.
The preparation of the novel crystalline form of the compound of the formula (I) according to the invention is effected, e.g., by the compound of the formula (I) in non-crystalline form being suspended in inert organic solvents, optionally in the presence of water, and being treated at elevated temperatures until it is quantita-tively converted into the crystalline modification, andthe resulting crystals of the crystalline modification then being separated off by customary methods and, to remove any solvent residues which may be present, dried Le A 29 305 - 2 -210848~
to constant weight at temperatures of +20C to +70C.
The duration of the conversion depends on the nature of the solvent and the temperature selected. As a rule, it amounts to several days to weeks.
Lower alcohols having 1 to 6 carbon atoms are preferably employed as solvents; ethanol or isopropanol is pre-ferably used. In this context, mixtures of the alcohols with water in the ratio of one part of alcohol to 20 parts of water, preferably of one part of alcohol to 10 parts of water, are very particularly preferred. The use of ethanol or isopropanolJwater mixtures in the ratio 1:8 is very particularly preferred.
The conversion of the non-crystalline form into the crystalline form of the compound of the formula (I) is usually effected by stirring or shaking the suspension at elevated temperatures.
The separation of the crystals from the water/solvent mixture takes place according to customary methods, such as, for example, by filtration, decanting off, centri-fugation or the like. Subsequently, the crystals aredried to constant mass at an elevated temperature, for example at +50C or in vacuo.
The complete conversion of the non-crystalline form into the crystalline modification is determined by DSC (dif-ferential scanning calorimetry), spectroscopic or Le A 29 305 - 3 -- 2~0~86 crystallographic methods.
A more rapid process, which is particularly suitable for preparing relatively large quantities of crystalline active compound, is achieved with the aid of seed crys-tals, by, for example, the non-crystalline active com-pound being suspended in a mixture of water and ethanol in the ratio 8:1, the suspension being heated to +70C, some seeds of the crystalline active compound being added, and the mixture being stirred for about 4 h until the non-crystalline active compound has been quantita tively converted into the crystalline active compound.
However~ if the time of stirring is extended, the com-plete conversion can also be effected at an elevated temperature below +70C, for example in a temperature range of ~40~ to +60C, or in other solvent mixtures, such as, for example, water and isopropanol, or in solvent mixtures with other mixture ratios, such as, for example, in mixtures of water and alcohol in the ratio of 15:1 to 25:1.
The crystalline modification of the (R)-(-)-2-cyclo-heptyl-N-methylsulfony1- [4-(2-quinolinylmethoxy)-phenyl]-acetamide according to the invention possesses a characteristic IR spectrum.
The thermogram of the crystalline modification according to the invention, recorded by means of DSC (differential scanning calorLmetry) under atmospheric pressure, shows an endothermic melting peak at 124-127C and thus differs Le A 29 305 - 4 -2108~6 unan~iguously from the thermograms of other forms of the active compound.
soth the X-ray diffractograms and the 13C solid NMR
spectra are characteristic of the crystalline modifica-tion according to the invention. The density of the crystalline (R)-(~)-2-cycloheptyl-N-methylsulfonyl- t4-(2-quino 1 inyl methoxy)-phenyl]-acetamide is 1.30 g/cm3.
The present invention also includes pharmaceutical preparations which, besides inert non-toxic pharmaceuti-cally suitable auxiliaries and vehicles, contain thecrystalline form of the compound of the formula (I) according to the invention, or which comprise the crys-talline modification of the compound of the formula (I), as well as processes for producing these preparations. In this context, solid drug forms and suspensions are to be mentioned as being preferred. The crystalline active compound is particularly suitable for preparing solid medicament~, e.g. in the form of tablets, pill8, coated tablets or capsules.
In these preparations, the novel crystalline modification of the compound of the formula (I) should be present in a concentration of 0.1 to 99.5~ by weight, preferably of 0.5 to 95~ by weight, of the total mixture.
As well as the crystalline modification of the compound of the formula (I), the pharmaceutical preparations may also contain other pharmaceutical active compounds.
Le A 29 305 - 5 _ 21~84~6 The abovementioned pharmaceutical preparations can be prepared in a customary manner by known methods, for example with one or more auxiliaries or vehicles.
Preparation examples Example 1 Preparation of seed crystals 1 g of non-crystalline active compound is suspended in a water/isopropanol mixture (8 ml:1 ml), and stirred at +50C for 14 days. The suspension is subsequently fil-tered and dried in vacuo to constant mass.
Example 2 Crystallisation by seeding 1 g of non-crystalline active compound is suspended in a water/ethanol mixture (8 ml:l ml), seeded with a few seed crystals and stirred at +70C for 4 hours. The suspension is subsequently filtered and dried to constant mass.
Le A 29 305 - 6 -
Claims (17)
1. (R)-(-)-2-Cycloheptyl-N-methylsulfonyl-[4-(2-quinoo-linylmethoxy)-phenyl]-acetamide of the formula in crystalline form.
2. Crystalline active compound according to claim 1 for therapeutic use.
3. A process for preparing the compound in crystalline form, which process comprises suspending non-crystalline (R)-(-)-2-cycloheptyl-N-methylsulfonyl-[4-(2-quinolinylmethoxy)-phenyl]-acetamide in an inert organic solvent at elevated temperature until conversion to the crystalline form of the compound has occurred.
4. A process according to claim 3 wherein water is also present in the solvent.
5. A process according to claim 4 wherein the solvent is a mixture of water and one or more lower alcohols having up to
6 carbon atoms.
6. A process according to claim 4 wherein the solvent is a mixture of ethanol and water.
6. A process according to claim 4 wherein the solvent is a mixture of ethanol and water.
7. A process according to claim 4 wherein the solvent is a mixture of isopropanol and water.
8. A process according to any one of claims 5 to 7 wherein one part of alcohol and up to 20 parts of water are employed.
9. A process according to any one of claims 3 to 7 wherein the compound is suspended at a temperature in the range of +40 to +70°C.
10. Process for preparing the crystalline active compound according to claim 1, characterised in that non-crystalline (R)-(-)-2-cycloheptyl-N-methylsulfonyl-[4-(2-quinolinylmethoxy)-phenyl]-acetamide is suspended in inert organic solvents, optionally in the presence of water, and treated at elevated temperatures until it is quantitatively converted into the crystalline modification, and the resulting crystals of the crystalline modification are then separated off by customary methods and, to remove any solvent residues which may be present, dried to constant weight at temperatures of +20 to +70°C.
11. Process according to claim 10, characterised in that mixtures of lower alcohols having up to 6 carbon atoms and water are employed.
12. Process according to claim 10, characterised in that ethanol/water mixtures or isopropanol/water mixtures are employed.
13. Process according to claim 10, characterised in that alcohol/water mixtures in the ratio of one part of alcohol to 20 parts of water are employed.
14. Use of the crystalline active compound according to claim 1 for preparing medicaments.
15. Use according to claim 14 for preparing solid medicaments.
16. Medicaments containing the crystalline active compound according to claim 1, together with a suitable diluent or carrier.
17. Process for preparing medicaments according to claim 16, characterised in that the crystalline active compound, optionally with the aid of customary auxiliaries and vehicles, is converted into an appropriate form for administration.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP4235133.2 | 1992-10-19 | ||
| DE4235133A DE4235133A1 (en) | 1992-10-19 | 1992-10-19 | Crystalline (R) - (-) - 2-cycloheptyl-N-methylsulfonyl- [4- (2-quinolinyl-methoxy) phenyl] acetamide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2108486A1 true CA2108486A1 (en) | 1994-04-20 |
Family
ID=6470759
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002108486A Abandoned CA2108486A1 (en) | 1992-10-19 | 1993-10-15 | Crystalline(r)-(-)-2-cycloheptyl-n-methylsulfonyl- [4-(2-quinolinyl-methoxy)-phenyl]-acetamide |
Country Status (4)
| Country | Link |
|---|---|
| EP (1) | EP0593976A1 (en) |
| JP (1) | JPH06192228A (en) |
| CA (1) | CA2108486A1 (en) |
| DE (1) | DE4235133A1 (en) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2167587T3 (en) | 1995-07-17 | 2002-05-16 | Warner Lambert Co | CRYSTAL FORM OF THE HEMICALCIC ACID SALT (R- (R *, R *)) - 2- (4-FLUOROPHENIL) -BETA, DELTA-DIHIDROXI-5- (1-METHYL) -3-PHENYL-4 - (( PHENYLAMINE) CARBONIL) -1H-PIRROL-1-HEPTANOIC (ATORVASTATIN). |
| GB2356139A (en) * | 1999-11-15 | 2001-05-16 | Bayer Ag | Use of substituted (quinolin-2-yl-methoxy)phenyl-acyl-sulphonamides and cyanamides for the treatment of diseases |
| TWI328006B (en) * | 2003-12-26 | 2010-08-01 | Nissan Chemical Ind Ltd | Crystal form of quinoline compound and process for its production |
| KR101266549B1 (en) * | 2006-10-20 | 2013-05-24 | 시노팜 싱가포르 피티이 리미티드 | Process for making crystalline anhydrous docetaxel |
| PT103661B (en) * | 2007-02-23 | 2010-09-07 | Hovione Farmaciencia S A | MINOCYCINE PREPARATION PROCESS CRYSTALLINE |
| JP2010540440A (en) | 2007-09-21 | 2010-12-24 | エピファニー バイオサイエンシズ， インク． | Valomaciclovir polymorph |
| AU2013362400B2 (en) * | 2012-12-22 | 2016-07-28 | Novo Nordisk A/S | Crystal form of compound used as mineralocorticoid receptor antagonist and preparation method therefor |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3900261A1 (en) * | 1988-05-31 | 1989-12-07 | Bayer Ag | SUBSTITUTED 4- (CHINOLIN-2-YL-METHOXY) PHENYL-ACETIC ACID DERIVATIVES |
| DE3916663A1 (en) * | 1989-05-23 | 1990-11-29 | Bayer Ag | SUBSTITUTED (CHINOLIN-2-YL-METHOXY) PHENYL-ACYL-SULPHONAMIDES AND CYANAMIDS, PROCESS FOR THEIR PREPARATION AND THEIR USE IN MEDICAMENTS |
| GB9027018D0 (en) * | 1990-12-12 | 1991-01-30 | Ici Plc | Heterocyclic compounds |
| IL100091A (en) * | 1990-12-12 | 1998-08-16 | Zeneca Ltd | Pharmaceutical compositions containing a physical form of n-[4-[5-(cyclopentyloxycarbonyl)amino-1-methyl indol-3-yl-methyl]-2-methylbenzenesulpho-namide and process for their preparation |
-
1992
- 1992-10-19 DE DE4235133A patent/DE4235133A1/en not_active Withdrawn
-
1993
- 1993-10-06 EP EP93116152A patent/EP0593976A1/en not_active Withdrawn
- 1993-10-15 JP JP5280680A patent/JPH06192228A/en active Pending
- 1993-10-15 CA CA002108486A patent/CA2108486A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| DE4235133A1 (en) | 1994-04-21 |
| EP0593976A1 (en) | 1994-04-27 |
| JPH06192228A (en) | 1994-07-12 |
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| Date | Code | Title | Description |
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| FZDE | Dead |