SK68399A3 - 2-imidazolinylaminoindole compound, pharmaceutical composition containing the same and use thereof - Google Patents

2-imidazolinylaminoindole compound, pharmaceutical composition containing the same and use thereof Download PDF

Info

Publication number: SK68399A3
Authority: SK; Slovakia
Prior art keywords: imidazolinylamino; unsubstituted; hydrogen; cyano; compounds
Prior art date: 1996-11-25

Application number

SK683-99A

Other languages

English (en)

Slovak (sk)

Inventor

Raymond Todd Henry

Russell James Sheldon

William Lee Seibel

Original Assignee

Procter & Gamble

Priority date (The priority date 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 date listed.)

1996-11-25

Filing date

1997-11-21

Publication date

2000-07-11

1997-11-21 Application filed by Procter & Gamble filed Critical Procter & Gamble

2000-07-11 Publication of SK68399A3 publication Critical patent/SK68399A3/sk

Links

-1 2-imidazolinylaminoindole compound Chemical class 0.000 title claims abstract description 50
239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 7
150000001875 compounds Chemical class 0.000 claims abstract description 187
150000003839 salts Chemical class 0.000 claims abstract description 39
239000001257 hydrogen Substances 0.000 claims abstract description 22
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 22
108060003345 Adrenergic Receptor Proteins 0.000 claims abstract description 17
102000017910 Adrenergic receptor Human genes 0.000 claims abstract description 17
125000003342 alkenyl group Chemical group 0.000 claims abstract description 16
125000000446 sulfanediyl group Chemical group *S* 0.000 claims abstract description 13
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 11
125000003545 alkoxy group Chemical group 0.000 claims abstract description 10
125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims abstract description 9
125000006698 (C1-C3) dialkylamino group Chemical group 0.000 claims abstract description 9
125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims abstract description 7
125000000304 alkynyl group Chemical group 0.000 claims abstract description 7
150000002148 esters Chemical class 0.000 claims abstract description 7
230000003287 optical effect Effects 0.000 claims abstract description 6
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims abstract description 5
150000001408 amides Chemical class 0.000 claims abstract description 5
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 5
125000000217 alkyl group Chemical group 0.000 claims abstract description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 4
241000124008 Mammalia Species 0.000 claims description 20
229910052736 halogen Inorganic materials 0.000 claims description 12
150000002367 halogens Chemical class 0.000 claims description 12
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
239000003937 drug carrier Substances 0.000 claims description 10
150000002431 hydrogen Chemical class 0.000 claims description 9
PCKPVGOLPKLUHR-UHFFFAOYSA-N OH-Indolxyl Natural products C1=CC=C2C(O)=CNC2=C1 PCKPVGOLPKLUHR-UHFFFAOYSA-N 0.000 claims description 6
239000003963 antioxidant agent Substances 0.000 claims description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 6
JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical compound C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 claims description 6
239000013543 active substance Substances 0.000 claims description 5
239000000384 adrenergic alpha-2 receptor agonist Substances 0.000 claims description 5
125000003282 alkyl amino group Chemical group 0.000 claims description 5
125000004414 alkyl thio group Chemical group 0.000 claims description 5
125000004663 dialkyl amino group Chemical group 0.000 claims description 5
XQVAUYTZTRCAQS-UHFFFAOYSA-N n-(4,5-dihydroimidazol-1-yl)-1h-indol-4-amine Chemical compound C1=NCCN1NC1=CC=CC2=C1C=CN2 XQVAUYTZTRCAQS-UHFFFAOYSA-N 0.000 claims description 5
QNJGKLTUONJRPU-UHFFFAOYSA-N n-(4,5-dihydroimidazol-1-yl)-7-methyl-1h-indol-6-amine Chemical compound C1=CC=2C=CNC=2C(C)=C1NN1CCN=C1 QNJGKLTUONJRPU-UHFFFAOYSA-N 0.000 claims description 5
239000003381 stabilizer Substances 0.000 claims description 5
UCIWJBLQGSHKFP-UHFFFAOYSA-N 6-(4,5-dihydroimidazol-1-ylamino)-7-methyl-1h-indole-3-carbonitrile Chemical compound C1=CC=2C(C#N)=CNC=2C(C)=C1NN1CCN=C1 UCIWJBLQGSHKFP-UHFFFAOYSA-N 0.000 claims description 4
239000003172 expectorant agent Substances 0.000 claims description 4
UTRJFTCXNCZWLQ-UHFFFAOYSA-N n-(4,5-dihydroimidazol-1-yl)-7-methyl-2,3-dihydro-1h-indol-4-amine Chemical compound C1=2CCNC=2C(C)=CC=C1NN1CCN=C1 UTRJFTCXNCZWLQ-UHFFFAOYSA-N 0.000 claims description 4
125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 3
GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 claims description 3
125000005843 halogen group Chemical group 0.000 claims description 3
210000003630 histaminocyte Anatomy 0.000 claims description 3
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125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 claims 1
150000001335 aliphatic alkanes Chemical class 0.000 claims 1
230000001387 anti-histamine Effects 0.000 claims 1
230000003078 antioxidant effect Effects 0.000 claims 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
PCHPORCSPXIHLZ-UHFFFAOYSA-N diphenhydramine hydrochloride Chemical compound [Cl-].C=1C=CC=CC=1C(OCC[NH+](C)C)C1=CC=CC=C1 PCHPORCSPXIHLZ-UHFFFAOYSA-N 0.000 claims 1
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239000004083 gastrointestinal agent Substances 0.000 claims 1
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SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 abstract description 12
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RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 abstract description 6
125000004093 cyano group Chemical group *C#N 0.000 abstract description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract description 4
125000000392 cycloalkenyl group Chemical group 0.000 abstract 3
125000001475 halogen functional group Chemical group 0.000 abstract 3
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VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 34
235000019441 ethanol Nutrition 0.000 description 32
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HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
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238000010898 silica gel chromatography Methods 0.000 description 19
125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 18
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CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 18
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TVZGQZOAPIZUBZ-UHFFFAOYSA-N tert-butyl 4-amino-7-methyl-2,3-dihydroindole-1-carboxylate Chemical compound CC1=CC=C(N)C2=C1N(C(=O)OC(C)(C)C)CC2 TVZGQZOAPIZUBZ-UHFFFAOYSA-N 0.000 description 1
VTCFJLPISNJVAT-UHFFFAOYSA-N tert-butyl 4-isothiocyanato-7-methyl-2,3-dihydroindole-1-carboxylate Chemical compound CC1=CC=C(N=C=S)C2=C1N(C(=O)OC(C)(C)C)CC2 VTCFJLPISNJVAT-UHFFFAOYSA-N 0.000 description 1
LMAOBFFBYOUPDG-UHFFFAOYSA-N tert-butyl 6-amino-7-methyl-2,3-dihydroindole-1-carboxylate Chemical compound C1=C(N)C(C)=C2N(C(=O)OC(C)(C)C)CCC2=C1 LMAOBFFBYOUPDG-UHFFFAOYSA-N 0.000 description 1
238000012956 testing procedure Methods 0.000 description 1
229960000278 theophylline Drugs 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
150000003573 thiols Chemical class 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
XFYDIVBRZNQMJC-UHFFFAOYSA-N tizanidine Chemical compound ClC=1C=CC2=NSN=C2C=1NC1=NCCN1 XFYDIVBRZNQMJC-UHFFFAOYSA-N 0.000 description 1
229960000488 tizanidine Drugs 0.000 description 1
235000010384 tocopherol Nutrition 0.000 description 1
229960001295 tocopherol Drugs 0.000 description 1
229930003799 tocopherol Natural products 0.000 description 1
239000011732 tocopherol Substances 0.000 description 1
229960001017 tolmetin Drugs 0.000 description 1
UPSPUYADGBWSHF-UHFFFAOYSA-N tolmetin Chemical compound C1=CC(C)=CC=C1C(=O)C1=CC=C(CC(O)=O)N1C UPSPUYADGBWSHF-UHFFFAOYSA-N 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
238000011200 topical administration Methods 0.000 description 1
229940100613 topical solution Drugs 0.000 description 1
231100000027 toxicology Toxicity 0.000 description 1
LLPOLZWFYMWNKH-UHFFFAOYSA-N trans-dihydrocodeinone Natural products C1C(N(CCC234)C)C2CCC(=O)C3OC2=C4C1=CC=C2OC LLPOLZWFYMWNKH-UHFFFAOYSA-N 0.000 description 1
229960005294 triamcinolone Drugs 0.000 description 1
GFNANZIMVAIWHM-OBYCQNJPSA-N triamcinolone Chemical compound O=C1C=C[C@]2(C)[C@@]3(F)[C@@H](O)C[C@](C)([C@@]([C@H](O)C4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 GFNANZIMVAIWHM-OBYCQNJPSA-N 0.000 description 1
ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
229960003223 tripelennamine Drugs 0.000 description 1
229960001128 triprolidine Drugs 0.000 description 1
CBEQULMOCCWAQT-WOJGMQOQSA-N triprolidine Chemical compound C1=CC(C)=CC=C1C(\C=1N=CC=CC=1)=C/CN1CCCC1 CBEQULMOCCWAQT-WOJGMQOQSA-N 0.000 description 1
PKIDNTKRVKSLDB-UHFFFAOYSA-K trisodium;2-hydroxypropane-1,2,3-tricarboxylate;hydrate Chemical compound O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O PKIDNTKRVKSLDB-UHFFFAOYSA-K 0.000 description 1
230000036269 ulceration Effects 0.000 description 1
208000027185 varicose disease Diseases 0.000 description 1
230000002792 vascular Effects 0.000 description 1
238000007631 vascular surgery Methods 0.000 description 1
210000005166 vasculature Anatomy 0.000 description 1
230000025033 vasoconstriction Effects 0.000 description 1
239000005526 vasoconstrictor agent Substances 0.000 description 1
208000001319 vasomotor rhinitis Diseases 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
201000002282 venous insufficiency Diseases 0.000 description 1
239000004034 viscosity adjusting agent Substances 0.000 description 1
239000003039 volatile agent Substances 0.000 description 1
239000012855 volatile organic compound Substances 0.000 description 1
239000001993 wax Substances 0.000 description 1
238000005303 weighing Methods 0.000 description 1
MWLSOWXNZPKENC-SSDOTTSWSA-N zileuton Chemical compound C1=CC=C2SC([C@H](N(O)C(N)=O)C)=CC2=C1 MWLSOWXNZPKENC-SSDOTTSWSA-N 0.000 description 1
229960005332 zileuton Drugs 0.000 description 1
229960000568 zipeprol Drugs 0.000 description 1
VSTNNAYSCJQCQI-UHFFFAOYSA-N zipeprol Chemical compound C=1C=CC=CC=1C(OC)CN(CC1)CCN1CC(O)C(OC)C1=CC=CC=C1 VSTNNAYSCJQCQI-UHFFFAOYSA-N 0.000 description 1
GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
- 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
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- 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
- A61K31/47—Quinolines; Isoquinolines
- A61K31/475—Quinolines; Isoquinolines having an indole ring, e.g. yohimbine, reserpine, strychnine, vinblastine
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/02—Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
- A—HUMAN NECESSITIES
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- A61P13/00—Drugs for disorders of the urinary system
- A61P13/08—Drugs for disorders of the urinary system of the prostate
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- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
- A—HUMAN NECESSITIES
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- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- A—HUMAN NECESSITIES
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- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/32—Alcohol-abuse
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- A61P25/36—Opioid-abuse
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P27/02—Ophthalmic agents
- A61P27/14—Decongestants or antiallergics
- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/02—Non-specific cardiovascular stimulants, e.g. drugs for syncope, antihypotensives
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Cardiology (AREA)
Neurology (AREA)
Heart & Thoracic Surgery (AREA)
Neurosurgery (AREA)
Biomedical Technology (AREA)
Epidemiology (AREA)
Addiction (AREA)
Psychiatry (AREA)
Ophthalmology & Optometry (AREA)
Hospice & Palliative Care (AREA)
Pain & Pain Management (AREA)
Urology & Nephrology (AREA)
Vascular Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

SK683-99A 1996-11-25 1997-11-21 2-imidazolinylaminoindole compound, pharmaceutical composition containing the same and use thereof SK68399A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US3177796P	1996-11-25	1996-11-25
PCT/US1997/020801 WO1998023610A1 (fr)	1996-11-25	1997-11-21	Composes 2-imidazolinylaminoindole convenant comme agonistes de l'adrenorecepteur alpha-2

Publications (1)

Publication Number	Publication Date
SK68399A3 true SK68399A3 (en)	2000-07-11

Family

ID=21861336

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK683-99A SK68399A3 (en)	1996-11-25	1997-11-21	2-imidazolinylaminoindole compound, pharmaceutical composition containing the same and use thereof

Country Status (23)

Country	Link
US (2)	US6162818A (fr)
EP (1)	EP0944621B1 (fr)
JP (1)	JP2001506981A (fr)
KR (1)	KR100395356B1 (fr)
CN (1)	CN1092652C (fr)
AR (1)	AR013875A1 (fr)
AT (1)	ATE275142T1 (fr)
AU (1)	AU735767B2 (fr)
BR (1)	BR9713542A (fr)
CA (1)	CA2271841C (fr)
CO (1)	CO4910149A1 (fr)
CZ (1)	CZ180599A3 (fr)
DE (1)	DE69730516T2 (fr)
ES (1)	ES2225998T3 (fr)
HU (1)	HUP9904215A3 (fr)
ID (1)	ID22812A (fr)
IL (1)	IL130024A (fr)
NO (1)	NO992470L (fr)
PE (1)	PE16299A1 (fr)
SK (1)	SK68399A3 (fr)
TR (1)	TR199901885T2 (fr)
WO (1)	WO1998023610A1 (fr)
ZA (1)	ZA9710577B (fr)

Families Citing this family (23)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5677321A (en)	1996-02-29	1997-10-14	Synaptic Pharmaceutical Corporation	5- and 6-(2-imidazolin-2-ylamino) and -(2-thiazolin-2-ylamino)-benzothiazoles as alpha-2 adrenergic ligands
ATE275142T1 (de) *	1996-11-25	2004-09-15	Procter & Gamble	2-imidazolinylaminoindol verbindungen als alpha-2 adrenoceptor agonisten
US5866579A (en) *	1997-04-11	1999-02-02	Synaptic Pharmaceutical Corporation	Imidazole and imidazoline derivatives and uses thereof
AU5960300A (en) *	1999-07-15	2001-02-05	Nps Allelix Corp.	Heterocyclic compounds for the treatment of migraine
WO2001040183A1 (fr) *	1999-12-03	2001-06-07	Alcon Universal Ltd.	1-aminoalkyl-1 h-indoles pour traiter le glaucome
US20030166732A1 (en) *	2002-02-27	2003-09-04	Boehringer Ingelheim Pharma Gmbh & Co. Kg	Ambroxol for the treatment of painful conditions in the mouth and pharyngeal cavity
DE60309598T2 (de) *	2002-06-24	2007-09-13	Schering Corp.	Als histamin-h3-antagonisten geeignete indolderivate
MXPA05004929A (es)	2002-11-07	2005-08-18	Akzo Nobel Nv	Indoles utiles en el tratamiento de enfermedades relacionadas a receptor de androgeno.
DE10332473A1 (de) *	2003-07-16	2005-02-03	Boehringer Ingelheim Pharma Gmbh & Co. Kg	Ambroxol für die Behandlung von Epilepsie
TW200602317A (en)	2004-04-23	2006-01-16	Akzo Nobel Nv	Novel androgens
ZA200804550B (en)	2005-11-09	2009-08-26	Combinatorx Inc	Methods, compositions, and kits for the treatment of medical conditions
TWI417099B (zh) *	2007-03-23	2013-12-01	Neuraxon Inc	具抑制一氧化氮合成酶活性之喹諾酮、四氫喹啉及其相關化合物
US20100203165A1 (en)	2008-08-01	2010-08-12	Gerald Horn	Compositions and methods for treatment of disorders or conditions of the eye
US20100197694A1 (en) *	2008-08-01	2010-08-05	Gerald Horn	Compositions and methods for treatment of diseases and conditions with increased vascular permeability
US20100202979A1 (en) *	2008-08-01	2010-08-12	Gerald Horn	Compositions and methods for treatment of pulmonary diseases and conditions
US12246013B2 (en)	2008-08-01	2025-03-11	Eye Therapies Llc	Vasoconstriction compositions and methods of use
US20110003823A1 (en) *	2008-08-01	2011-01-06	Alpha Synergy Development, Inc.	Compositions and methods for treatment of diseases and conditions associated with vasodilation and/or vascular leakage
US8952011B2 (en)	2008-08-01	2015-02-10	Eye Therapies Llc	Compositions and methods for the treatment of nasal conditions
ES2518418T3 (es) *	2008-08-01	2014-11-05	Eye Therapies Llc	Composiciones de vasoconstricción y métodos de uso
US20100196286A1 (en) *	2008-12-01	2010-08-05	Armer Thomas A	Inhalation delivery methods and devices
WO2010074753A1 (fr)	2008-12-23	2010-07-01	Map Pharmaceuticals, Inc.	Dispositifs d'inhalation et procédés associés pour administration de composés hypnotiques sédatifs
US8987270B2 (en)	2009-07-27	2015-03-24	Eye Therapies Llc	Formulations of selective alpha-2 agonists and methods of use thereof
CN107628981B (zh) *	2017-10-31	2019-07-30	威海市妇女儿童医院	一种肉桂酰基吲哚啉化合物及其制备青光眼药物的应用

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
BE795970A (fr) *	1972-02-29	1973-08-27	Pfizer	Nouveaux derives de quinoleine, quinoxaline et quinazoline er composition pharmaceutiques les contenant
CH632268A5 (de) *	1977-01-14	1982-09-30	Sandoz Ag	Verfahren zur herstellung von neuen heterocyclylaminoderivaten.
US4398028A (en) *	1977-01-14	1983-08-09	Sandoz Ltd.	Bicyclic heterocyclic amino derivatives
US5091528A (en) *	1990-09-12	1992-02-25	Allergan, Inc.	6- or 7- (2-imino-2-imidazolidine)-1,4-benzoxazines as α adrenergic agents
US5478858A (en) *	1993-12-17	1995-12-26	The Procter & Gamble Company	5-(2-imidazolinylamino) benzimidazole compounds useful as alpha-2 adrenoceptor agonists
US5677321A (en) *	1996-02-29	1997-10-14	Synaptic Pharmaceutical Corporation	5- and 6-(2-imidazolin-2-ylamino) and -(2-thiazolin-2-ylamino)-benzothiazoles as alpha-2 adrenergic ligands
ATE275142T1 (de) *	1996-11-25	2004-09-15	Procter & Gamble	2-imidazolinylaminoindol verbindungen als alpha-2 adrenoceptor agonisten

1997
- 1997-11-21 AT AT97948289T patent/ATE275142T1/de not_active IP Right Cessation
- 1997-11-21 ES ES97948289T patent/ES2225998T3/es not_active Expired - Lifetime
- 1997-11-21 CA CA002271841A patent/CA2271841C/fr not_active Expired - Fee Related
- 1997-11-21 SK SK683-99A patent/SK68399A3/sk unknown
- 1997-11-21 BR BR9713542-9A patent/BR9713542A/pt not_active IP Right Cessation
- 1997-11-21 AU AU54380/98A patent/AU735767B2/en not_active Ceased
- 1997-11-21 CN CN97180036A patent/CN1092652C/zh not_active Expired - Fee Related
- 1997-11-21 TR TR1999/01885T patent/TR199901885T2/xx unknown
- 1997-11-21 DE DE69730516T patent/DE69730516T2/de not_active Expired - Lifetime
- 1997-11-21 CZ CZ991805A patent/CZ180599A3/cs unknown
- 1997-11-21 JP JP52469398A patent/JP2001506981A/ja active Pending
- 1997-11-21 KR KR10-1999-7004535A patent/KR100395356B1/ko not_active Expired - Fee Related
- 1997-11-21 HU HU9904215A patent/HUP9904215A3/hu unknown
- 1997-11-21 ID IDW990403D patent/ID22812A/id unknown
- 1997-11-21 WO PCT/US1997/020801 patent/WO1998023610A1/fr not_active Ceased
- 1997-11-21 IL IL13002497A patent/IL130024A/en not_active IP Right Cessation
- 1997-11-21 EP EP97948289A patent/EP0944621B1/fr not_active Expired - Lifetime
- 1997-11-24 CO CO97068609A patent/CO4910149A1/es unknown
- 1997-11-25 AR ARP970105526A patent/AR013875A1/es unknown
- 1997-11-25 ZA ZA9710577A patent/ZA9710577B/xx unknown
- 1997-11-25 PE PE1997001069A patent/PE16299A1/es not_active Application Discontinuation
1999
- 1999-04-13 US US09/290,731 patent/US6162818A/en not_active Expired - Lifetime
- 1999-05-21 NO NO992470A patent/NO992470L/no not_active Application Discontinuation
2000
- 2000-10-17 US US09/690,992 patent/US6395764B1/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
EP0944621B1 (fr)	2004-09-01
HUP9904215A3 (en)	2002-01-28
WO1998023610A1 (fr)	1998-06-04
US6162818A (en)	2000-12-19
DE69730516T2 (de)	2005-09-01
CN1238771A (zh)	1999-12-15
AR013875A1 (es)	2001-01-31
CO4910149A1 (es)	2000-04-24
PE16299A1 (es)	1999-03-12
AU5438098A (en)	1998-06-22
KR100395356B1 (ko)	2003-08-21
KR20000069088A (ko)	2000-11-25
BR9713542A (pt)	2000-01-25
ATE275142T1 (de)	2004-09-15
CA2271841C (fr)	2003-07-08
DE69730516D1 (de)	2004-10-07
EP0944621A1 (fr)	1999-09-29
NO992470L (no)	1999-07-26
IL130024A0 (en)	2000-02-29
HUP9904215A2 (hu)	2000-06-28
JP2001506981A (ja)	2001-05-29
AU735767B2 (en)	2001-07-12
CN1092652C (zh)	2002-10-16
CA2271841A1 (fr)	1998-06-04
ES2225998T3 (es)	2005-03-16
CZ180599A3 (cs)	1999-11-17
US6395764B1 (en)	2002-05-28
TR199901885T2 (xx)	1999-10-21
ID22812A (id)	1999-12-09
IL130024A (en)	2002-12-01
NO992470D0 (no)	1999-05-21
ZA9710577B (en)	1998-06-25

Publication	Publication Date	Title
KR100395356B1 (ko)	2003-08-21	알파-2 아드레날린수용체 아고니스트로서 유용한 2-이미다졸리닐아미노인돌 화합물
AU730369B2 (en)	2001-03-08	Guanidinyl heterocycle compounds useful as alpha-2 adrenoceptor agonists
US6117871A (en)	2000-09-12	6-(2-imidazolinylamino)quinoxaline compounds useful as alpha-2 adrenoceptor agonists
US5804587A (en)	1998-09-08	6-(2-imidazolinylamino) quinolines useful as alpha-2 adrenoceptor agonists
AU736992B2 (en)	2001-08-09	2-imidazolinylaminobenzoxazole compounds useful as alpha-2 adrenoceptor agonists
US5914342A (en)	1999-06-22	2-imidazolinylamino heterocyclic compounds useful as alpha-2 adrenoceptor agonists
US6172095B1 (en)	2001-01-09	Guanidinylamino heterocycle compounds useful as alpha-2 adrenoceptor agonists
EP0944601B1 (fr)	2003-02-12	Composes heterocycliques guanidinylamino utiles en tant qu'agonistes de l'adrenorecepteur alpha-2
US6306877B1 (en)	2001-10-23	Guanidinylamino heterocycle compounds useful as alpha-2 adrenoceptor agonists
KR20010006440A (ko)	2001-01-26	알파-2 아드레날린수용체 아고니스트로서 유용한 5-(2-이미다졸리닐아미노)벤즈이미다졸 화합물
KR20000069104A (ko)	2000-11-25	알파-2 아드레날린수용체 아고니스트로서 유용한 2-이미다졸리닐아미노인다졸 화합물
MXPA99004843A (en)	2000-04-24	Guanidinyl heterocycle compounds useful as alpha-2 adrenoceptor agonists