DK175233B1 - Serotonin-antagonister til behandling af sår - Google Patents

Serotonin-antagonister til behandling af sår Download PDF

Info

Publication number: DK175233B1
Authority: DK; Denmark
Prior art keywords: group; hydrogen; formula; alkyl; halogen
Prior art date: 1986-09-22

Application number

DK198704951A

Other languages

Danish (da)

English (en)

Other versions

DK495187D0 (da

DK495187A (da

Inventor

Leo Alfons Andre Ooms

Anne-Dominique Alice Y Degryse

Original Assignee

Janssen Pharmaceutica Nv

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.)

1986-09-22

Filing date

1987-09-21

Publication date

2004-07-19

1987-09-21 Application filed by Janssen Pharmaceutica Nv filed Critical Janssen Pharmaceutica Nv

1987-09-21 Publication of DK495187D0 publication Critical patent/DK495187D0/da

1988-03-23 Publication of DK495187A publication Critical patent/DK495187A/da

2004-07-19 Application granted granted Critical

2004-07-19 Publication of DK175233B1 publication Critical patent/DK175233B1/da

Links

206010052428 Wound Diseases 0.000 title claims abstract description 39
208000027418 Wounds and injury Diseases 0.000 title claims abstract description 39
239000003420 antiserotonin agent Substances 0.000 title abstract description 5
229940082988 antihypertensives serotonin antagonists Drugs 0.000 title description 2
239000000203 mixture Substances 0.000 claims abstract description 30
230000029663 wound healing Effects 0.000 claims abstract description 20
150000001875 compounds Chemical class 0.000 claims abstract description 19
239000003814 drug Substances 0.000 claims abstract description 15
239000004480 active ingredient Substances 0.000 claims abstract description 11
229910052739 hydrogen Inorganic materials 0.000 claims description 25
239000001257 hydrogen Substances 0.000 claims description 25
238000002360 preparation method Methods 0.000 claims description 17
-1 cyano, hydroxy Chemical group 0.000 claims description 14
229910052736 halogen Inorganic materials 0.000 claims description 13
150000002367 halogens Chemical class 0.000 claims description 13
239000007788 liquid Substances 0.000 claims description 13
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
238000000034 method Methods 0.000 claims description 11
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
125000000217 alkyl group Chemical group 0.000 claims description 9
239000002674 ointment Substances 0.000 claims description 8
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 7
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
239000002253 acid Substances 0.000 claims description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
239000000843 powder Substances 0.000 claims description 5
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 4
229910052760 oxygen Inorganic materials 0.000 claims description 4
150000003839 salts Chemical class 0.000 claims description 4
229910052717 sulfur Inorganic materials 0.000 claims description 4
239000006071 cream Substances 0.000 claims description 3
241000021559 Dicerandra Species 0.000 claims description 2
235000010654 Melissa officinalis Nutrition 0.000 claims description 2
JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 2
125000003277 amino group Chemical group 0.000 claims description 2
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
239000000865 liniment Substances 0.000 claims description 2
239000012669 liquid formulation Substances 0.000 claims description 2
125000004430 oxygen atom Chemical group O* 0.000 claims description 2
239000008247 solid mixture Substances 0.000 claims description 2
239000000725 suspension Substances 0.000 claims description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims 3
DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 claims 1
150000001412 amines Chemical class 0.000 claims 1
125000006332 fluoro benzoyl group Chemical group 0.000 claims 1
235000015110 jellies Nutrition 0.000 claims 1
239000008274 jelly Substances 0.000 claims 1
QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 abstract description 12
238000004519 manufacturing process Methods 0.000 abstract description 5
230000003042 antagnostic effect Effects 0.000 abstract description 3
229940076279 serotonin Drugs 0.000 abstract description 3
238000009472 formulation Methods 0.000 description 12
FPCCSQOGAWCVBH-UHFFFAOYSA-N ketanserin Chemical compound C1=CC(F)=CC=C1C(=O)C1CCN(CCN2C(C3=CC=CC=C3NC2=O)=O)CC1 FPCCSQOGAWCVBH-UHFFFAOYSA-N 0.000 description 10
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
229960005417 ketanserin Drugs 0.000 description 9
238000003756 stirring Methods 0.000 description 9
229940079593 drug Drugs 0.000 description 6
230000035876 healing Effects 0.000 description 5
VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 4
241001465754 Metazoa Species 0.000 description 4
239000000645 desinfectant Substances 0.000 description 4
230000000694 effects Effects 0.000 description 4
208000015181 infectious disease Diseases 0.000 description 4
239000004615 ingredient Substances 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
HSHXDCVZWHOWCS-UHFFFAOYSA-N N'-hexadecylthiophene-2-carbohydrazide Chemical compound CCCCCCCCCCCCCCCCNNC(=O)c1cccs1 HSHXDCVZWHOWCS-UHFFFAOYSA-N 0.000 description 3
229920002043 Pluronic® L 35 Polymers 0.000 description 3
RVGRUAULSDPKGF-UHFFFAOYSA-N Poloxamer Chemical compound C1CO1.CC1CO1 RVGRUAULSDPKGF-UHFFFAOYSA-N 0.000 description 3
208000025865 Ulcer Diseases 0.000 description 3
239000005557 antagonist Substances 0.000 description 3
239000003242 anti bacterial agent Substances 0.000 description 3
229940121363 anti-inflammatory agent Drugs 0.000 description 3
239000002260 anti-inflammatory agent Substances 0.000 description 3
229940088710 antibiotic agent Drugs 0.000 description 3
239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 3
229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 3
235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 3
231100000397 ulcer Toxicity 0.000 description 3
108091032151 5-hydroxytryptamine receptor family Proteins 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
206010015150 Erythema Diseases 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
241000700159 Rattus Species 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical compound [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
231100000321 erythema Toxicity 0.000 description 2
YQEMORVAKMFKLG-UHFFFAOYSA-N glycerine monostearate Natural products CCCCCCCCCCCCCCCCCC(=O)OC(CO)CO YQEMORVAKMFKLG-UHFFFAOYSA-N 0.000 description 2
SVUQHVRAGMNPLW-UHFFFAOYSA-N glycerol monostearate Natural products CCCCCCCCCCCCCCCCC(=O)OCC(O)CO SVUQHVRAGMNPLW-UHFFFAOYSA-N 0.000 description 2
238000000265 homogenisation Methods 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
125000003386 piperidinyl group Chemical group 0.000 description 2
229940068918 polyethylene glycol 400 Drugs 0.000 description 2
229940057838 polyethylene glycol 4000 Drugs 0.000 description 2
239000000243 solution Substances 0.000 description 2
KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
238000001356 surgical procedure Methods 0.000 description 2
238000009827 uniform distribution Methods 0.000 description 2
125000006619 (C1-C6) dialkylamino group Chemical group 0.000 description 1
101150072531 10 gene Proteins 0.000 description 1
NPQHIBFBMYRBRL-UHFFFAOYSA-N 2,3-dihydroxybutanedioic acid;1h-quinazoline-2,4-dione Chemical compound OC(=O)C(O)C(O)C(O)=O.C1=CC=C2C(=O)NC(=O)NC2=C1 NPQHIBFBMYRBRL-UHFFFAOYSA-N 0.000 description 1
LODHFNUFVRVKTH-ZHACJKMWSA-N 2-hydroxy-n'-[(e)-3-phenylprop-2-enoyl]benzohydrazide Chemical compound OC1=CC=CC=C1C(=O)NNC(=O)\C=C\C1=CC=CC=C1 LODHFNUFVRVKTH-ZHACJKMWSA-N 0.000 description 1
WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-aminosalicylic acid Chemical compound NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 description 1
KBIWNQVZKHSHTI-UHFFFAOYSA-N 4-n,4-n-dimethylbenzene-1,4-diamine;oxalic acid Chemical compound OC(=O)C(O)=O.CN(C)C1=CC=C(N)C=C1 KBIWNQVZKHSHTI-UHFFFAOYSA-N 0.000 description 1
102000040125 5-hydroxytryptamine receptor family Human genes 0.000 description 1
206010002091 Anaesthesia Diseases 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
102000008186 Collagen Human genes 0.000 description 1
108010035532 Collagen Proteins 0.000 description 1
201000004624 Dermatitis Diseases 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
102000014630 G protein-coupled serotonin receptor activity proteins Human genes 0.000 description 1
206010019233 Headaches Diseases 0.000 description 1
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Natural products OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
YGSDEFSMJLZEOE-UHFFFAOYSA-N Salicylic acid Natural products OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 1
206010041899 Stab wound Diseases 0.000 description 1
239000002390 adhesive tape Substances 0.000 description 1
125000004448 alkyl carbonyl group Chemical group 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
230000037005 anaesthesia Effects 0.000 description 1
230000036592 analgesia Effects 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
230000006793 arrhythmia Effects 0.000 description 1
206010003119 arrhythmia Diseases 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
208000010668 atopic eczema Diseases 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
229940092714 benzenesulfonic acid Drugs 0.000 description 1
KMGARVOVYXNAOF-UHFFFAOYSA-N benzpiperylone Chemical compound C1CN(C)CCC1N1C(=O)C(CC=2C=CC=CC=2)=C(C=2C=CC=CC=2)N1 KMGARVOVYXNAOF-UHFFFAOYSA-N 0.000 description 1
229950007647 benzpiperylone Drugs 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
229920001400 block copolymer Polymers 0.000 description 1
230000037396 body weight Effects 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
230000001684 chronic effect Effects 0.000 description 1
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 1
229920001436 collagen Polymers 0.000 description 1
239000007933 dermal patch Substances 0.000 description 1
238000011161 development Methods 0.000 description 1
230000018109 developmental process Effects 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
210000002950 fibroblast Anatomy 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 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
239000000499 gel Substances 0.000 description 1
238000000227 grinding Methods 0.000 description 1
231100000869 headache Toxicity 0.000 description 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 description 1
125000001183 hydrocarbyl group Chemical group 0.000 description 1
230000008595 infiltration Effects 0.000 description 1
238000001764 infiltration Methods 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
210000000265 leukocyte Anatomy 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000001630 malic acid Substances 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
239000000463 material Substances 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
238000002156 mixing Methods 0.000 description 1
DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 description 1
239000006072 paste Substances 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
230000002093 peripheral effect Effects 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
125000005936 piperidyl group Chemical group 0.000 description 1
229920001451 polypropylene glycol Polymers 0.000 description 1
230000035755 proliferation Effects 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
NYJWYCAHJRGKMI-UHFFFAOYSA-N pyrido[1,2-a]pyrimidin-4-one Chemical compound C1=CC=CN2C(=O)C=CN=C21 NYJWYCAHJRGKMI-UHFFFAOYSA-N 0.000 description 1
239000000018 receptor agonist Substances 0.000 description 1
229940044601 receptor agonist Drugs 0.000 description 1
230000008929 regeneration Effects 0.000 description 1
238000011069 regeneration method Methods 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
229930195734 saturated hydrocarbon Natural products 0.000 description 1
239000003369 serotonin 5-HT3 receptor antagonist Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
229960005137 succinic acid Drugs 0.000 description 1
210000000115 thoracic cavity Anatomy 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
230000000699 topical effect Effects 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
238000002054 transplantation Methods 0.000 description 1
239000003357 wound healing promoting agent Substances 0.000 description 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders

Landscapes

Health & Medical Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Chemical & Material Sciences (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Life Sciences & Earth Sciences (AREA)
Epidemiology (AREA)
General Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Dermatology (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Plural Heterocyclic Compounds (AREA)
Dental Preparations (AREA)
Treatment Of Water By Ion Exchange (AREA)
Vending Machines For Individual Products (AREA)

DK198704951A 1986-09-22 1987-09-21 Serotonin-antagonister til behandling af sår DK175233B1 (da)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US90999186A	1986-09-22	1986-09-22
US90999186		1986-09-22

Publications (3)

Publication Number	Publication Date
DK495187D0 DK495187D0 (da)	1987-09-21
DK495187A DK495187A (da)	1988-03-23
DK175233B1 true DK175233B1 (da)	2004-07-19

Family

ID=25428159

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DK198704951A DK175233B1 (da)	1986-09-22	1987-09-21	Serotonin-antagonister til behandling af sår

Country Status (18)

Country	Link
EP (1)	EP0268309B1 (de)
JP (1)	JPH0655682B2 (de)
KR (1)	KR950013759B1 (de)
AT (1)	ATE146077T1 (de)
AU (1)	AU610082B2 (de)
CA (1)	CA1302271C (de)
DE (1)	DE3751974T2 (de)
DK (1)	DK175233B1 (de)
ES (1)	ES2094718T3 (de)
GR (1)	GR3022390T3 (de)
IE (1)	IE81148B1 (de)
IL (1)	IL83956A (de)
NO (1)	NO873934L (de)
NZ (1)	NZ221880A (de)
PH (1)	PH23594A (de)
PT (1)	PT85766B (de)
SG (1)	SG47757A1 (de)
ZA (1)	ZA877084B (de)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3855513T2 (de) *	1987-10-28	1997-01-09	Pro Neuron Inc	Acyl deoxyribonukleosid-derivate und deren verwendungen
NZ228447A (en) *	1988-03-28	1990-08-28	Janssen Pharmaceutica Nv	Cosmetic or pharmaceutical composition possessing serotonin antogonistic activity
US5703088A (en) *	1989-08-21	1997-12-30	Beth Israel Deaconess Medical Center, Inc.	Topical application of spiperone or derivatives thereof for treatment of pathological conditions associated with immune responses
WO1991002527A1 (en) *	1989-08-21	1991-03-07	Beth Israel Hospital Association	Method and composition for the treatment of cutaneous, ocular, and mucosal hypersensitivity, inflammation, and hyperproliferative conditions using topical preparations of serotonin antagonists
IT1249678B (it) *	1991-07-12	1995-03-09	Ciro Costagliola	Collirio per il trattamento della ipertensione oculare
US5693645A (en) *	1992-12-23	1997-12-02	Beth Israel Deaconess Medical Center, Inc.	Use of spiperone or spiperone derivatives as immunosuppressant agents
SE2250051A1 (en) *	2022-01-20	2023-07-21	Amidea Sweden Ab	New pharmaceutical composition and uses thereof

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4335127A (en) *	1979-01-08	1982-06-15	Janssen Pharmaceutica, N.V.	Piperidinylalkyl quinazoline compounds, composition and method of use
US4342870A (en) *	1980-03-28	1982-08-03	Janssen Pharmaceutica N.V.	Novel 3-(1-piperidinylalkyl)-4H-pyrido[1,2-a]pyrimidin-4-one derivatives
US4443451A (en) *	1981-07-15	1984-04-17	Janssen Pharmaceutica N.V.	Bicyclic pyrimidin-5-one derivatives
FR2531083B1 (fr) *	1982-06-29	1986-11-28	Sandoz Sa	Nouveaux derives de la piperidine, leur preparation et leur utilisation comme medicaments

1987
- 1987-09-18 ES ES87201784T patent/ES2094718T3/es not_active Expired - Lifetime
- 1987-09-18 SG SG1996004222A patent/SG47757A1/en unknown
- 1987-09-18 AT AT87201784T patent/ATE146077T1/de not_active IP Right Cessation
- 1987-09-18 DE DE3751974T patent/DE3751974T2/de not_active Expired - Lifetime
- 1987-09-18 EP EP87201784A patent/EP0268309B1/de not_active Expired - Lifetime
- 1987-09-21 NO NO873934A patent/NO873934L/no unknown
- 1987-09-21 NZ NZ221880A patent/NZ221880A/xx unknown
- 1987-09-21 DK DK198704951A patent/DK175233B1/da not_active IP Right Cessation
- 1987-09-21 ZA ZA877084A patent/ZA877084B/xx unknown
- 1987-09-21 IL IL83956A patent/IL83956A/xx not_active IP Right Cessation
- 1987-09-21 JP JP62235044A patent/JPH0655682B2/ja not_active Expired - Lifetime
- 1987-09-21 AU AU78690/87A patent/AU610082B2/en not_active Expired
- 1987-09-21 CA CA000547362A patent/CA1302271C/en not_active Expired - Lifetime
- 1987-09-21 IE IE254087A patent/IE81148B1/en not_active IP Right Cessation
- 1987-09-22 PH PH35840A patent/PH23594A/en unknown
- 1987-09-22 KR KR1019870010505A patent/KR950013759B1/ko not_active Expired - Lifetime
- 1987-09-22 PT PT85766A patent/PT85766B/pt unknown
1997
- 1997-01-29 GR GR960403397T patent/GR3022390T3/el unknown

Also Published As

Publication number	Publication date
PT85766B (pt)	1991-02-08
PT85766A (en)	1987-10-01
EP0268309A3 (de)	1990-04-11
JPS63146819A (ja)	1988-06-18
JPH0655682B2 (ja)	1994-07-27
ES2094718T3 (es)	1997-02-01
KR880003627A (ko)	1988-05-28
AU7869087A (en)	1988-03-24
GR3022390T3 (en)	1997-04-30
IE81148B1 (en)	2000-05-03
EP0268309A2 (de)	1988-05-25
KR950013759B1 (ko)	1995-11-15
SG47757A1 (en)	1998-04-17
IL83956A (en)	1992-05-25
DK495187D0 (da)	1987-09-21
DK495187A (da)	1988-03-23
DE3751974D1 (de)	1997-01-23
DE3751974T2 (de)	1997-04-10
IE872540L (en)	1988-03-22
NO873934L (no)	1988-03-23
NO873934D0 (no)	1987-09-21
EP0268309B1 (de)	1996-12-11
NZ221880A (en)	1990-07-26
ZA877084B (en)	1989-04-26
PH23594A (en)	1989-09-11
CA1302271C (en)	1992-06-02
ATE146077T1 (de)	1996-12-15
AU610082B2 (en)	1991-05-16

Legal Events

Date	Code	Title	Description
2007-10-08	PUP	Patent expired

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JP2000128724A (ja)	2000-05-09	皮膚外用剤
JPS60116616A (ja)	1985-06-24	化粧料
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