CA1201066A - N-¬3,5-dichloro-4-(2-imidazolidinylideneamino)- phenyl|-acetamide solutions for lowering intraocular pressure - Google Patents
N-¬3,5-dichloro-4-(2-imidazolidinylideneamino)- phenyl|-acetamide solutions for lowering intraocular pressureInfo
- Publication number
- CA1201066A CA1201066A CA000415190A CA415190A CA1201066A CA 1201066 A CA1201066 A CA 1201066A CA 000415190 A CA000415190 A CA 000415190A CA 415190 A CA415190 A CA 415190A CA 1201066 A CA1201066 A CA 1201066A
- Authority
- CA
- Canada
- Prior art keywords
- dichloro
- imidazolidinylidene
- imidazolidinylideneamino
- iop
- diethyl
- 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.)
- Expired
Links
- 230000004410 intraocular pressure Effects 0.000 title abstract description 15
- 239000000243 solution Substances 0.000 claims description 42
- 150000001875 compounds Chemical class 0.000 claims description 41
- 150000003839 salts Chemical class 0.000 claims description 10
- 208000010412 Glaucoma Diseases 0.000 claims 1
- 239000000030 antiglaucoma agent Substances 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- UYOCYPVWZNEXKU-UHFFFAOYSA-N n-[3,5-dichloro-4-(4,5-dihydro-1h-imidazol-2-ylamino)phenyl]acetamide Chemical compound ClC1=CC(NC(=O)C)=CC(Cl)=C1NC1=NCCN1 UYOCYPVWZNEXKU-UHFFFAOYSA-N 0.000 abstract 1
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 14
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- CVABOWNITQPOSP-UHFFFAOYSA-N n-(4-amino-3,5-dichlorophenyl)-2,2,2-trichloroacetamide Chemical compound NC1=C(Cl)C=C(NC(=O)C(Cl)(Cl)Cl)C=C1Cl CVABOWNITQPOSP-UHFFFAOYSA-N 0.000 description 4
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- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- SFZPZOUCJLKYIW-UHFFFAOYSA-N Cl.CCC1=C(NC(C)=O)C(CC)=CC(N=C2NCCN2)=C1 Chemical compound Cl.CCC1=C(NC(C)=O)C(CC)=CC(N=C2NCCN2)=C1 SFZPZOUCJLKYIW-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- YQEZLKZALYSWHR-UHFFFAOYSA-N Ketamine Chemical compound C=1C=CC=C(Cl)C=1C1(NC)CCCCC1=O YQEZLKZALYSWHR-UHFFFAOYSA-N 0.000 description 1
- 241000282560 Macaca mulatta Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- 206010030043 Ocular hypertension Diseases 0.000 description 1
- 206010039897 Sedation Diseases 0.000 description 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
- UCTLHLZWKJIXJI-LXIBVNSESA-N [(3s,8r,9s,10r,13s,14s)-17-chloro-16-formyl-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15-decahydro-1h-cyclopenta[a]phenanthren-3-yl] acetate Chemical compound C([C@@H]12)C[C@]3(C)C(Cl)=C(C=O)C[C@H]3[C@@H]1CC=C1[C@]2(C)CC[C@H](OC(=O)C)C1 UCTLHLZWKJIXJI-LXIBVNSESA-N 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 229940087458 alcaine Drugs 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000037444 atrophy Effects 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 229960004217 benzyl alcohol Drugs 0.000 description 1
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006172 buffering agent Substances 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 238000011097 chromatography purification Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 235000008504 concentrate Nutrition 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- BIXZHMJUSMUDOQ-UHFFFAOYSA-N dichloran Chemical compound NC1=C(Cl)C=C([N+]([O-])=O)C=C1Cl BIXZHMJUSMUDOQ-UHFFFAOYSA-N 0.000 description 1
- SXUMXUHCGDHAEG-UHFFFAOYSA-N ethyl 3,5-dichloro-4-formamidobenzoate Chemical compound CCOC(=O)C1=CC(Cl)=C(NC=O)C(Cl)=C1 SXUMXUHCGDHAEG-UHFFFAOYSA-N 0.000 description 1
- MIDALAPASRDTOZ-UHFFFAOYSA-N ethyl 4-amino-3,5-dichlorobenzoate Chemical compound CCOC(=O)C1=CC(Cl)=C(N)C(Cl)=C1 MIDALAPASRDTOZ-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 210000001105 femoral artery Anatomy 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 150000003948 formamides Chemical class 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- ATADHKWKHYVBTJ-UHFFFAOYSA-N hydron;4-[1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol;chloride Chemical compound Cl.CNCC(O)C1=CC=C(O)C(O)=C1 ATADHKWKHYVBTJ-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 1
- 229960003299 ketamine Drugs 0.000 description 1
- 208000018769 loss of vision Diseases 0.000 description 1
- 231100000864 loss of vision Toxicity 0.000 description 1
- 229960003390 magnesium sulfate Drugs 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- QOSYCWFRMSWYOV-UHFFFAOYSA-N n-(2,6-dichloro-4-cyanophenyl)formamide Chemical compound ClC1=CC(C#N)=CC(Cl)=C1NC=O QOSYCWFRMSWYOV-UHFFFAOYSA-N 0.000 description 1
- NDTCYFFOCHVXFG-UHFFFAOYSA-N n-[3,5-dichloro-4-(4,5-dihydro-1h-imidazol-2-ylamino)phenyl]formamide Chemical compound ClC1=CC(NC=O)=CC(Cl)=C1N=C1NCCN1 NDTCYFFOCHVXFG-UHFFFAOYSA-N 0.000 description 1
- DJZMDTSNCZDIDI-UHFFFAOYSA-N n-[3-(4,5-dihydro-1h-imidazol-2-ylamino)-2,4-diethylphenyl]acetamide Chemical compound CCC1=CC=C(NC(C)=O)C(CC)=C1N=C1NCCN1 DJZMDTSNCZDIDI-UHFFFAOYSA-N 0.000 description 1
- PMULBNXDZRZHGP-UHFFFAOYSA-N n-[4-(4,5-dihydro-1h-imidazol-2-ylamino)-3,5-diethylphenyl]-n-methylacetamide Chemical compound CCC1=CC(N(C)C(C)=O)=CC(CC)=C1N=C1NCCN1 PMULBNXDZRZHGP-UHFFFAOYSA-N 0.000 description 1
- 210000003733 optic disk Anatomy 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 229960001412 pentobarbital Drugs 0.000 description 1
- WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 230000000649 photocoagulation Effects 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 230000000452 restraining effect Effects 0.000 description 1
- 230000028527 righting reflex Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000036280 sedation Effects 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 238000012453 sprague-dawley rat model Methods 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 210000001585 trabecular meshwork Anatomy 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 230000004393 visual impairment Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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 to ring carbon atoms
- C07D233/44—Nitrogen atoms not forming part of a nitro radical
- C07D233/50—Nitrogen atoms not forming part of a nitro radical with carbocyclic radicals directly attached to said nitrogen atoms
-
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Ophthalmology & Optometry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Fertilizers (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA000458039A CA1194418A (en) | 1981-11-20 | 1984-07-03 | 2-(trisubstituted phenylimino)-imidazoline compositions for lowering intraocular pressure |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US32336981A | 1981-11-20 | 1981-11-20 | |
| US323,369 | 1981-11-20 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000458039A Division CA1194418A (en) | 1981-11-20 | 1984-07-03 | 2-(trisubstituted phenylimino)-imidazoline compositions for lowering intraocular pressure |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1201066A true CA1201066A (en) | 1986-02-25 |
Family
ID=23258921
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000415190A Expired CA1201066A (en) | 1981-11-20 | 1982-11-09 | N-¬3,5-dichloro-4-(2-imidazolidinylideneamino)- phenyl|-acetamide solutions for lowering intraocular pressure |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP0081924B1 (enEXAMPLES) |
| JP (1) | JPS58116417A (enEXAMPLES) |
| AT (1) | ATE18006T1 (enEXAMPLES) |
| CA (1) | CA1201066A (enEXAMPLES) |
| DE (1) | DE3269242D1 (enEXAMPLES) |
| NL (1) | NL950008I2 (enEXAMPLES) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2549049B1 (fr) * | 1983-07-13 | 1986-06-20 | Chauvin Blache Lab | Nouvelles amidines, leur procede de preparation et leur application therapeutique |
| EP0236636A3 (en) * | 1986-02-07 | 1988-12-07 | Alcon Laboratories, Inc. | Use of clonidine derivatives for the preparation of ocular hemostatic agents |
| FR2592042B1 (fr) * | 1985-12-19 | 1988-03-25 | Ile De France | Nouveaux ortho-anisamides, leur procede d'obtention, et leurs applications therapeutiques |
| US4801617A (en) * | 1987-04-06 | 1989-01-31 | Leclerc Gerard | Iminoimidazolidines useful in lowering intraocular pressure |
| US5304569A (en) * | 1989-11-13 | 1994-04-19 | Orion-Yhtyma Oy | Compositions and their use in lowering intraocular pressure |
| US5124154A (en) * | 1990-06-12 | 1992-06-23 | Insite Vision Incorporated | Aminosteroids for ophthalmic use |
| US5340572A (en) * | 1993-02-08 | 1994-08-23 | Insite Vision Incorporated | Alkaline ophthalmic suspensions |
| DE19514579A1 (de) | 1995-04-20 | 1996-10-24 | Boehringer Ingelheim Kg | Verwendung von alpha¶1¶¶L¶-Agonisten zur Behandlung der Harninkontinenz |
| US6602897B2 (en) | 2000-10-14 | 2003-08-05 | Boehringer Ingelheim Pharma Kg | m-Amino-phenylimino-imidazolidine derivatives for treating urinary incontinence |
| IL155338A0 (en) * | 2000-10-14 | 2003-11-23 | Boehringer Ingelheim Pharma | Novel m-amino-phenylimino-imidazolidine derivatives for treating urinary incontinence |
| CN100335053C (zh) * | 2005-02-18 | 2007-09-05 | 山东鲁抗辰欣药业有限公司 | 一种药物制剂及其制备方法 |
| GB2466622A (en) * | 2008-12-23 | 2010-06-30 | Trinity College Dublin | Alpha2-Adrenoceptor Ligands |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3636219A (en) * | 1964-03-02 | 1972-01-18 | Du Pont | Anticholinergic compositions containing certain thiazolines or imidazolines |
| DE1670274A1 (de) * | 1966-10-31 | 1970-07-16 | Boehringer Sohn Ingelheim | Neues Verfahren zur Herstellung von 2-Arylamino-1,3-diazacycloalkenen-(2) |
| AT285599B (de) * | 1968-06-21 | 1970-11-10 | Boehringer Sohn Ingelheim | Verfahren zur Herstellung von neuen trisubstituierten 2-Arylaminoimidazolinen und ihren Salzen |
| BE759125A (fr) * | 1969-11-19 | 1971-05-18 | Boehringer Sohn Ingelheim | Nouvelles n-allyl-2-arylamino-imidazolines-(2) substituees et procedes pour les fabriquer |
| BE759126A (fr) * | 1969-11-19 | 1971-05-18 | Boehringer Sohn Ingelheim | Nouvelles n-cycloalcoyl-arylamino-imidazolines-(2) substituees et procedes pour les fabriquer |
| GB1595412A (en) * | 1976-12-14 | 1981-08-12 | Boots Co Ltd | Method for control of pests attacking animals |
| DE2806811A1 (de) * | 1978-02-17 | 1979-08-23 | Boehringer Sohn Ingelheim | Neue substituierte 2-phenylimino- imidazolidine, deren saeureadditionssalze, diese enthaltene arzneimittel und verfahren zur herstellung derselben |
| DE2806775A1 (de) * | 1978-02-17 | 1979-08-30 | Boehringer Sohn Ingelheim | Neue substituierte 2-phenylimino- imidazolidine deren saeureadditionssalze, diese enthaltende arzneimittel und verfahren zur herstellung derselben |
| US4287201A (en) * | 1980-03-03 | 1981-09-01 | Merck & Co., Inc. | Anovulatory method and chicken feed compositions |
| EP0043659B1 (en) * | 1980-07-09 | 1985-02-06 | Beecham Group Plc | Clonidine derivatives useful in the treatment of diarrhoea |
-
1982
- 1982-11-09 CA CA000415190A patent/CA1201066A/en not_active Expired
- 1982-11-19 AT AT82306188T patent/ATE18006T1/de active
- 1982-11-19 DE DE8282306188T patent/DE3269242D1/de not_active Expired
- 1982-11-19 EP EP82306188A patent/EP0081924B1/en not_active Expired
- 1982-11-20 JP JP57204428A patent/JPS58116417A/ja active Granted
-
1995
- 1995-05-08 NL NL950008C patent/NL950008I2/nl unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP0081924B1 (en) | 1986-02-19 |
| DE3269242D1 (en) | 1986-03-27 |
| NL950008I2 (nl) | 1996-12-02 |
| ATE18006T1 (de) | 1986-03-15 |
| EP0081924A1 (en) | 1983-06-22 |
| JPS58116417A (ja) | 1983-07-11 |
| JPH0453846B2 (enEXAMPLES) | 1992-08-27 |
| NL950008I1 (nl) | 1995-06-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |