CA2132007A1 - Method for reducing intraocular pressure in the mammalian eye by administration of muscarinic antagonists - Google Patents
Method for reducing intraocular pressure in the mammalian eye by administration of muscarinic antagonistsInfo
- Publication number
- CA2132007A1 CA2132007A1 CA002132007A CA2132007A CA2132007A1 CA 2132007 A1 CA2132007 A1 CA 2132007A1 CA 002132007 A CA002132007 A CA 002132007A CA 2132007 A CA2132007 A CA 2132007A CA 2132007 A1 CA2132007 A1 CA 2132007A1
- Authority
- CA
- Canada
- Prior art keywords
- alpha
- methyl
- piperidinyl
- dihydro
- benzodiazepin
- 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.)
- Granted
Links
- 229940121948 Muscarinic receptor antagonist Drugs 0.000 title abstract 3
- 239000003149 muscarinic antagonist Substances 0.000 title abstract 3
- 230000004410 intraocular pressure Effects 0.000 title 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 3
- 239000008194 pharmaceutical composition Substances 0.000 abstract 3
- PWGJDPKCLMLPJW-UHFFFAOYSA-N 1,8-diaminooctane Chemical compound NCCCCCCCCN PWGJDPKCLMLPJW-UHFFFAOYSA-N 0.000 abstract 1
- IXXCPZGOFVCPCH-UHFFFAOYSA-N 1-cyclohexyl-1-phenyl-4-piperidin-1-ylbut-2-yn-1-ol Chemical compound C1CCCCC1C(C=1C=CC=CC=1)(O)C#CCN1CCCCC1 IXXCPZGOFVCPCH-UHFFFAOYSA-N 0.000 abstract 1
- VSWPGAIWKHPTKX-UHFFFAOYSA-N 1-methyl-10-[2-(4-methyl-1-piperazinyl)-1-oxoethyl]-5H-thieno[3,4-b][1,5]benzodiazepin-4-one Chemical compound C1CN(C)CCN1CC(=O)N1C2=CC=CC=C2NC(=O)C2=CSC(C)=C21 VSWPGAIWKHPTKX-UHFFFAOYSA-N 0.000 abstract 1
- UBRKDAVQCKZSPO-UHFFFAOYSA-N 11-[2-[2-(diethylaminomethyl)-1-piperidinyl]-1-oxoethyl]-5H-pyrido[2,3-b][1,4]benzodiazepin-6-one Chemical compound CCN(CC)CC1CCCCN1CC(=O)N1C2=NC=CC=C2NC(=O)C2=CC=CC=C21 UBRKDAVQCKZSPO-UHFFFAOYSA-N 0.000 abstract 1
- RLUNJKJUFRFYJM-UHFFFAOYSA-N 11-[2-[2-(diethylaminomethyl)piperidin-1-yl]acetyl]-5h-benzo[b][1,4]benzodiazepin-6-one Chemical compound CCN(CC)CC1CCCCN1CC(=O)N1C2=CC=CC=C2C(=O)NC2=CC=CC=C21 RLUNJKJUFRFYJM-UHFFFAOYSA-N 0.000 abstract 1
- BCUGCHZRMKTPMU-UHFFFAOYSA-N 11-[2-[4-[4-(diethylamino)butyl]-1-piperidinyl]-1-oxoethyl]-5H-pyrido[2,3-b][1,4]benzodiazepin-6-one Chemical compound C1CC(CCCCN(CC)CC)CCN1CC(=O)N1C2=NC=CC=C2NC(=O)C2=CC=CC=C21 BCUGCHZRMKTPMU-UHFFFAOYSA-N 0.000 abstract 1
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 abstract 1
- IPEMCIBPDYCJLO-UHFFFAOYSA-N 5-[(3,5,5,8,8-pentamethyl-6,7-dihydronaphthalen-2-yl)methyl]-n-(2,4,6-trimethoxyphenyl)furan-2-carboxamide Chemical compound COC1=CC(OC)=CC(OC)=C1NC(=O)C(O1)=CC=C1CC1=CC(C(CCC2(C)C)(C)C)=C2C=C1C IPEMCIBPDYCJLO-UHFFFAOYSA-N 0.000 abstract 1
- MZDYABXXPZNUCT-OAQYLSRUSA-N AF-DX 384 Chemical compound CCCN(CCC)C[C@H]1CCCCN1CCNC(=O)N1C2=NC=CC=C2NC(=O)C2=CC=CC=C21 MZDYABXXPZNUCT-OAQYLSRUSA-N 0.000 abstract 1
- 208000010412 Glaucoma Diseases 0.000 abstract 1
- FMPNFDSPHNUFOS-HQEQRHKESA-N Himbacine Natural products C(/[C@@H]1[C@H]2CCCC[C@@H]2C[C@@H]2C(=O)O[C@H]([C@H]12)C)=C\[C@@H]1CCC[C@H](C)N1C FMPNFDSPHNUFOS-HQEQRHKESA-N 0.000 abstract 1
- FMPNFDSPHNUFOS-UHFFFAOYSA-N N-Methyl-himandravin Natural products C12C(C)OC(=O)C2CC2CCCCC2C1C=CC1CCCC(C)N1C FMPNFDSPHNUFOS-UHFFFAOYSA-N 0.000 abstract 1
- 206010030043 Ocular hypertension Diseases 0.000 abstract 1
- HWHLPVGTWGOCJO-UHFFFAOYSA-N Trihexyphenidyl Chemical group C1CCCCC1C(C=1C=CC=CC=1)(O)CCN1CCCCC1 HWHLPVGTWGOCJO-UHFFFAOYSA-N 0.000 abstract 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- VSSAZBXXNIABDN-UHFFFAOYSA-N cyclohexylmethanol Chemical compound OCC1CCCCC1 VSSAZBXXNIABDN-UHFFFAOYSA-N 0.000 abstract 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- FMPNFDSPHNUFOS-LPJDIUFZSA-N himbacine Chemical compound C(/[C@@H]1[C@H]2CCCC[C@@H]2C[C@@H]2C(=O)O[C@H]([C@H]12)C)=C\[C@H]1CCC[C@H](C)N1C FMPNFDSPHNUFOS-LPJDIUFZSA-N 0.000 abstract 1
- RPMBYDYUVKEZJA-UHFFFAOYSA-N methoctramine Chemical compound COC1=CC=CC=C1CNCCCCCCNCCCCCCCCNCCCCCCNCC1=CC=CC=C1OC RPMBYDYUVKEZJA-UHFFFAOYSA-N 0.000 abstract 1
- LBXOPAJGAXATCZ-UHFFFAOYSA-N n-[2-[2-[(dipropylamino)methyl]piperidin-1-yl]ethyl]-6-oxo-5h-pyrido[2,3-b][1,4]benzodiazepine-11-carboxamide;methanesulfonic acid Chemical compound CS(O)(=O)=O.CCCN(CCC)CC1CCCCN1CCNC(=O)N1C2=NC=CC=C2NC(=O)C2=CC=CC=C21 LBXOPAJGAXATCZ-UHFFFAOYSA-N 0.000 abstract 1
- RMHMFHUVIITRHF-UHFFFAOYSA-N pirenzepine Chemical compound C1CN(C)CCN1CC(=O)N1C2=NC=CC=C2NC(=O)C2=CC=CC=C21 RMHMFHUVIITRHF-UHFFFAOYSA-N 0.000 abstract 1
- 229960004633 pirenzepine Drugs 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- QYETZOYLEWPRIX-UHFFFAOYSA-N pyrido[2,3-b][1,4]benzodiazepin-6-one Chemical compound O=C1N=C2C=CC=NC2=NC2=CC=CC=C12 QYETZOYLEWPRIX-UHFFFAOYSA-N 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 229950004351 telenzepine Drugs 0.000 abstract 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 abstract 1
- ZMZWUZSDXBEXGE-UHFFFAOYSA-N thieno[3,4-b][1,5]benzodiazepin-4-one Chemical compound O=C1N=C2C=CC=CC2=NC2=CSC=C12 ZMZWUZSDXBEXGE-UHFFFAOYSA-N 0.000 abstract 1
- 229960001032 trihexyphenidyl Drugs 0.000 abstract 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 abstract 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
Pharmaceutical compositions and a method are disclosed for treating glaucoma and/or ocular hypertension in the mammalian eye by administering to the mammalian eye the pharmaceutical composition of the invention which contains as the active ingredient one or more muscarinic antagonist compounds. Examples of muscarinic antagonists utilized in the pharmaceutical composition and method of treatment are: 10H-thieno(3,4-b)(1,5)benzodiazepin-10-one 4,9-dihydro-3-methyl-4-((4-methyl-1-piperazinyl) acetyl) (telenzepine); 5,11-dihydro-11(4'-methyl-1'-piperazinyl)-acetyl]-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one (pirenzepine): racemic 11-[[2-(Diethylamino)methyl]-1-piperidinyl]-acetyl]-5,11-dihydro-5H-pyrido[2,3-b][1,4]benzodiazepin-6-one (AF-DX 116); dextrorotatory 11-[[2-(Diethylamino)methyl]-1-piperidinyl]-acetyl]-5,11-dihydro-6H-pyrido[2,3-b][1,4]
benzodiazepin-6-one (AF-DX 250); an ophthalmically acceptable salt of 4-diphenylacetoxy-1,1-dimethyl piperidine (4-DAMP);
.alpha.-cyclohexyl, -.alpha.-phenyl-1-piperidinepropanol (trihexyphenidyl);
cyclohexanemethanol, .alpha.-phenyl, .alpha.-[3-(1-piperidinyl)-1-propynyl (hexbutinol); 6H-pyrido[2,3-b][1,4]benzodiazepin-6-one, 11-[[4-[4-(diethylamino)butyl]-l-piperidinyl]acetyl]-5,11-dihydro (AQ-RA
741); 11-H-pyrido[2,3-b][1,4]benzodiazepine-11-carboxamide, N-(2-(2-[(dipropylamino)methyl]-1-piperidinyl]ethyl]-5-, 6-dihydro-6-oxo, monomethanesulfonate (AF-DX 384); 1,8-octanediamine, N,N'-bis[6-]((2-methoxyphenyl)methyl]amino]
hexyl]-tetrahy-drochloride (methoctramine) and naphto[2,3-c]furan-1(3H)-one, 4-2-(1,6-dimethyl-2-piperidinyl)ethenyl]decahydro-3-methyl-, (3S-(3 .alpha., 3a .alpha., 4 .beta.[1E,2(2R*,6S*)],4a .beta., 8a .alpha., 9a .alpha.]] (himbacine).
benzodiazepin-6-one (AF-DX 250); an ophthalmically acceptable salt of 4-diphenylacetoxy-1,1-dimethyl piperidine (4-DAMP);
.alpha.-cyclohexyl, -.alpha.-phenyl-1-piperidinepropanol (trihexyphenidyl);
cyclohexanemethanol, .alpha.-phenyl, .alpha.-[3-(1-piperidinyl)-1-propynyl (hexbutinol); 6H-pyrido[2,3-b][1,4]benzodiazepin-6-one, 11-[[4-[4-(diethylamino)butyl]-l-piperidinyl]acetyl]-5,11-dihydro (AQ-RA
741); 11-H-pyrido[2,3-b][1,4]benzodiazepine-11-carboxamide, N-(2-(2-[(dipropylamino)methyl]-1-piperidinyl]ethyl]-5-, 6-dihydro-6-oxo, monomethanesulfonate (AF-DX 384); 1,8-octanediamine, N,N'-bis[6-]((2-methoxyphenyl)methyl]amino]
hexyl]-tetrahy-drochloride (methoctramine) and naphto[2,3-c]furan-1(3H)-one, 4-2-(1,6-dimethyl-2-piperidinyl)ethenyl]decahydro-3-methyl-, (3S-(3 .alpha., 3a .alpha., 4 .beta.[1E,2(2R*,6S*)],4a .beta., 8a .alpha., 9a .alpha.]] (himbacine).
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/853,374 | 1992-03-18 | ||
| US07/853,374 US5716952A (en) | 1992-03-18 | 1992-03-18 | Method for reducing intraocular pressure in the mammalian eye by administration of muscarinic antagonists |
| PCT/US1993/002403 WO1993018772A1 (en) | 1992-03-18 | 1993-03-16 | Method for reducing intraocular pressure in the mammalian eye by administration of muscarinic antagonists |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2132007A1 true CA2132007A1 (en) | 1993-09-30 |
| CA2132007C CA2132007C (en) | 2006-07-18 |
Family
ID=36693987
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002132007A Expired - Fee Related CA2132007C (en) | 1992-03-18 | 1993-03-16 | Method for reducing intraocular pressure in the mammalian eye by administration of muscarinic antagonists |
Country Status (1)
| Country | Link |
|---|---|
| CA (1) | CA2132007C (en) |
-
1993
- 1993-03-16 CA CA002132007A patent/CA2132007C/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CA2132007C (en) | 2006-07-18 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| ATE219367T1 (en) | METHOD FOR LOWERING THE INTERNAL OCCULAR PRESSURE IN THE EYES OF MAMMALS USING MUSCARINO ANTAGONISTS | |
| US6534496B1 (en) | Thermogenic composition and benzazepine thermogenics | |
| US5096890B1 (en) | Pyrrolidine derivatives | |
| US5741791A (en) | Method of reducing blood glucose | |
| AU668159B2 (en) | Pharmaceutical compounds | |
| JP2002521429A5 (en) | ||
| KR20020016926A (en) | Chemokine receptor antagonists and methods of use therefor | |
| CA2283663A1 (en) | Benzocycloheptathiophene compounds | |
| EP0607864A2 (en) | Tricyclic condensed heterocyclic compounds for the treatment of senile dementic | |
| JPH0692405B2 (en) | Tricyclic pyridine derivative | |
| CA2132007A1 (en) | Method for reducing intraocular pressure in the mammalian eye by administration of muscarinic antagonists | |
| AU2007230981A1 (en) | New therapeutic combinations for the treatment or prevention of psychotic disorders | |
| US4710504A (en) | Anti-depressant spiro hexahydro arylquinolizine derivatives, composition, and method of use therefor | |
| AU5217186A (en) | Tricyclic compounds, compositions containing such compounds, processes for their preparation and method of treatment therewith | |
| AU2007315932A1 (en) | A pharmaceutical composition having antipsychotic, antidepressant or antiepiieptic activity with reduced side effect | |
| EA007903B1 (en) | Pharmaceutical composition of a pde4 or a pde3/4 inhibitor and a histamine receptor antagonist | |
| US3454579A (en) | Imidazo(1,5-a)quinolin-1-one and thione derivatives | |
| US5321021A (en) | Tricyclic pyridine derivatives | |
| EP0468562B1 (en) | Tetrahydropyridinyl substituted tricyclic derivatives with dopamine antagonistic activity | |
| US5286722A (en) | Tetrahydropyridinyldibenzazepine derivatives | |
| EP0204254A2 (en) | Substituted hexahydro arylquinolizines, processes for their preparation and pharmaceutical compositions containing them | |
| US4824849A (en) | α2 -adrenoceptor antagonistic arylquinolizines | |
| RU99123631A (en) | SALTS OF OPTICALLY ACTIVE SULFOXIDE DERIVATIVE |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |