LV10094B - Novel pilocarpine derivatives and process for their preparation - Google Patents

Novel pilocarpine derivatives and process for their preparation Download PDF

Info

Publication number: LV10094B
Authority: LV; Latvia
Prior art keywords: formula; compound; acid; bispilocarpate; mmoles
Prior art date: 1990-11-30

Application number

LVP-93-436A

Other languages

English (en)

Latvian (lv)

Other versions

LV10094A (lv

Inventor

Tomi J Rvinen

Pekka Peura

Pekka Suhonen

Arto Urtti

Hannu Hanhij Rvi

Esko Pohjala

Original Assignee

Leiras Oy

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.)

1990-11-30

Filing date

1993-05-28

Publication date

1995-02-20

1993-05-28 Application filed by Leiras Oy filed Critical Leiras Oy

1994-05-10 Publication of LV10094A publication Critical patent/LV10094A/xx

1995-02-20 Publication of LV10094B publication Critical patent/LV10094B/en

Links

238000000034 method Methods 0.000 title claims description 27
238000002360 preparation method Methods 0.000 title claims description 17
230000008569 process Effects 0.000 title claims description 7
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239000001257 hydrogen Substances 0.000 claims abstract description 15
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150000001875 compounds Chemical class 0.000 claims description 102
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PWAXUOGZOSVGBO-UHFFFAOYSA-N adipoyl chloride Chemical compound ClC(=O)CCCCC(Cl)=O PWAXUOGZOSVGBO-UHFFFAOYSA-N 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
150000001299 aldehydes Chemical class 0.000 description 1
239000003513 alkali Substances 0.000 description 1
150000004996 alkyl benzenes Chemical class 0.000 description 1
125000000304 alkynyl group Chemical group 0.000 description 1
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
125000005228 aryl sulfonate group Chemical group 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
239000002585 base Substances 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
229940073608 benzyl chloride Drugs 0.000 description 1
125000002619 bicyclic group Chemical group 0.000 description 1
239000004305 biphenyl Substances 0.000 description 1
235000010290 biphenyl Nutrition 0.000 description 1
238000009835 boiling Methods 0.000 description 1
230000036471 bradycardia Effects 0.000 description 1
208000006218 bradycardia Diseases 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
125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 1
DVECBJCOGJRVPX-UHFFFAOYSA-N butyryl chloride Chemical compound CCCC(Cl)=O DVECBJCOGJRVPX-UHFFFAOYSA-N 0.000 description 1
125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
125000002837 carbocyclic group Chemical group 0.000 description 1
150000001718 carbodiimides Chemical class 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
230000004087 circulation Effects 0.000 description 1
210000000795 conjunctiva Anatomy 0.000 description 1
230000008602 contraction Effects 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000006071 cream Substances 0.000 description 1
125000000392 cycloalkenyl group Chemical group 0.000 description 1
125000004977 cycloheptylene group Chemical group 0.000 description 1
125000004979 cyclopentylene group Chemical group 0.000 description 1
125000006255 cyclopropyl carbonyl group Chemical group [H]C1([H])C([H])([H])C1([H])C(*)=O 0.000 description 1
125000004980 cyclopropylene group Chemical group 0.000 description 1
125000003493 decenyl group Chemical group [H]C([*])=C([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000005070 decynyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C#C* 0.000 description 1
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000013583 drug formulation Substances 0.000 description 1
230000009977 dual effect Effects 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
230000007515 enzymatic degradation Effects 0.000 description 1
238000006345 epimerization reaction Methods 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
210000000744 eyelid Anatomy 0.000 description 1
125000004030 farnesyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
238000009472 formulation Methods 0.000 description 1
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000006038 hexenyl group Chemical group 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
125000005980 hexynyl group Chemical group 0.000 description 1
125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
230000007794 irritation Effects 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
150000002632 lipids Chemical class 0.000 description 1
150000002634 lipophilic molecules Chemical class 0.000 description 1
239000007788 liquid Substances 0.000 description 1
238000004811 liquid chromatography Methods 0.000 description 1
239000003120 macrolide antibiotic agent Substances 0.000 description 1
229940041033 macrolides Drugs 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
230000014759 maintenance of location Effects 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
238000005259 measurement Methods 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
239000012528 membrane Substances 0.000 description 1
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
230000005012 migration Effects 0.000 description 1
238000013508 migration Methods 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
238000005065 mining Methods 0.000 description 1
150000002763 monocarboxylic acids Chemical class 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
125000005187 nonenyl group Chemical group C(=CCCCCCCC)* 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000005071 nonynyl group Chemical group C(#CCCCCCCC)* 0.000 description 1
125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000005069 octynyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C#C* 0.000 description 1
WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
BOWDPJFAGBREQM-UHFFFAOYSA-N pent-1-ene;pent-2-ene Chemical compound CCCC=C.CCC=CC BOWDPJFAGBREQM-UHFFFAOYSA-N 0.000 description 1
YVOFTMXWTWHRBH-UHFFFAOYSA-N pentanedioyl dichloride Chemical compound ClC(=O)CCCC(Cl)=O YVOFTMXWTWHRBH-UHFFFAOYSA-N 0.000 description 1
XGISHOFUAFNYQF-UHFFFAOYSA-N pentanoyl chloride Chemical compound CCCCC(Cl)=O XGISHOFUAFNYQF-UHFFFAOYSA-N 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
125000005981 pentynyl group Chemical group 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
229940095606 pilocar Drugs 0.000 description 1
125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
230000009467 reduction Effects 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
229910000077 silane Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
239000000725 suspension Substances 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
229940086542 triethylamine Drugs 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
239000008096 xylene Substances 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
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
- 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
- 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
- A61P27/06—Antiglaucoma agents or miotics
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Ophthalmology & Optometry (AREA)
Pharmacology & Pharmacy (AREA)
General Health & Medical Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

LVP-93-436A 1990-11-30 1993-05-28 Novel pilocarpine derivatives and process for their preparation LV10094B (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FI905930A FI98815C (fi)	1990-11-30	1990-11-30	Menetelmä uusien, farmakologisesti käyttökelpoisten bispilokarpiinihapon esterijohdannaisten valmistamiseksi
PCT/FI1991/000359 WO1992009583A1 (en)	1990-11-30	1991-11-27	Novel pilocarpine derivatives and process for their preparation

Publications (2)

Publication Number	Publication Date
LV10094A LV10094A (lv)	1994-05-10
LV10094B true LV10094B (en)	1995-02-20

Family

ID=8531500

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
LVP-93-436A LV10094B (en)	1990-11-30	1993-05-28	Novel pilocarpine derivatives and process for their preparation

Country Status (19)

Country	Link
EP (1)	EP0559700B1 (de)
JP (1)	JP3094232B2 (de)
KR (1)	KR930703264A (de)
AT (1)	ATE192144T1 (de)
AU (1)	AU664958B2 (de)
CA (1)	CA2096444A1 (de)
CZ (1)	CZ282229B6 (de)
DE (1)	DE69132143T2 (de)
EE (1)	EE9400143A (de)
FI (1)	FI98815C (de)
HU (1)	HUT67273A (de)
LT (1)	LT3532B (de)
LV (1)	LV10094B (de)
NO (1)	NO304228B1 (de)
NZ (1)	NZ240781A (de)
PL (2)	PL168715B1 (de)
RU (1)	RU2100352C1 (de)
SK (1)	SK52393A3 (de)
WO (1)	WO1992009583A1 (de)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO1993024466A1 (en) *	1992-05-29	1993-12-09	Leiras Oy	Novel pilocarpine derivatives and process for their preparation
GB9310965D0 (en) *	1993-05-27	1993-07-14	Ucb Sa	2-hydroxy-3-(1h-imidazol-4-yl)alkyl)benzenecarboximidamides
AU6973094A (en) *	1993-06-24	1995-01-17	Leiras Oy	Composition for ophthalmic use
SE501482C2 (sv)	1993-06-24	1995-02-27	Leiras Oy	Komposition för topisk administration av bispilokarpinsyradiestrar till ögat i form av en vattenlösning
SE9302201D0 (sv)	1993-06-24	1993-06-24	Leiras Oy	Composition for ophthalmic use
DE4334135A1 (de) *	1993-10-07	1995-04-13	Merck Patent Gmbh	Verfahren zur Herstellung von Pilocarpin-Derivaten

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4061722A (en)	1976-04-26	1977-12-06	Interx Research Corporation	Selected quaternary ammonium salts of pilocarpine useful in reducing intraocular pressure in warm-blooded animals
IL69593A (en) *	1982-09-17	1988-09-30	Bundegaard Hans	Pilocarpine prodrugs,their preparation and pharmaceutical compositions containing them

1990
- 1990-11-30 FI FI905930A patent/FI98815C/fi not_active IP Right Cessation
1991
- 1991-11-27 PL PL91308270A patent/PL168715B1/pl unknown
- 1991-11-27 EP EP91920512A patent/EP0559700B1/de not_active Expired - Lifetime
- 1991-11-27 RU RU93041054/04A patent/RU2100352C1/ru not_active IP Right Cessation
- 1991-11-27 AU AU89398/91A patent/AU664958B2/en not_active Ceased
- 1991-11-27 HU HU9301569A patent/HUT67273A/hu unknown
- 1991-11-27 SK SK523-93A patent/SK52393A3/sk unknown
- 1991-11-27 CA CA002096444A patent/CA2096444A1/en not_active Abandoned
- 1991-11-27 KR KR1019930701611A patent/KR930703264A/ko not_active Withdrawn
- 1991-11-27 PL PL91299375A patent/PL167773B1/pl unknown
- 1991-11-27 CZ CS931025A patent/CZ282229B6/cs not_active IP Right Cessation
- 1991-11-27 WO PCT/FI1991/000359 patent/WO1992009583A1/en not_active Ceased
- 1991-11-27 AT AT91920512T patent/ATE192144T1/de not_active IP Right Cessation
- 1991-11-27 JP JP04500392A patent/JP3094232B2/ja not_active Expired - Fee Related
- 1991-11-27 DE DE69132143T patent/DE69132143T2/de not_active Expired - Fee Related
- 1991-11-28 NZ NZ240781A patent/NZ240781A/xx unknown
1993
- 1993-05-28 LV LVP-93-436A patent/LV10094B/en unknown
- 1993-05-28 NO NO931960A patent/NO304228B1/no not_active IP Right Cessation
- 1993-05-28 LT LTIP577A patent/LT3532B/lt not_active IP Right Cessation
1994
- 1994-11-16 EE EE9400143A patent/EE9400143A/xx unknown

Also Published As

Publication number	Publication date
KR930703264A (ko)	1993-11-29
NO931960L (no)	1993-05-28
PL168715B1 (pl)	1996-03-29
ATE192144T1 (de)	2000-05-15
CA2096444A1 (en)	1992-05-31
DE69132143D1 (de)	2000-05-31
HUT67273A (en)	1995-03-28
JPH06504270A (ja)	1994-05-19
HU9301569D0 (en)	1993-09-28
JP3094232B2 (ja)	2000-10-03
RU2100352C1 (ru)	1997-12-27
CZ102593A3 (en)	1994-04-13
EE9400143A (et)	1995-12-15
LV10094A (lv)	1994-05-10
LTIP577A (en)	1994-12-27
NO304228B1 (no)	1998-11-16
LT3532B (en)	1995-11-27
AU8939891A (en)	1992-06-25
FI905930A0 (fi)	1990-11-30
CZ282229B6 (cs)	1997-06-11
FI905930A7 (fi)	1992-05-31
WO1992009583A1 (en)	1992-06-11
NO931960D0 (no)	1993-05-28
SK52393A3 (en)	1994-01-12
PL167773B1 (pl)	1995-11-30
FI98815C (fi)	1997-08-25
NZ240781A (en)	1993-12-23
FI98815B (fi)	1997-05-15
EP0559700A1 (de)	1993-09-15
DE69132143T2 (de)	2000-12-14
EP0559700B1 (de)	2000-04-26
AU664958B2 (en)	1995-12-07

Publication	Publication Date	Title
US4593044A (en)	1986-06-03	Injectable solution for the treatment of inflammations
US6589959B1 (en)	2003-07-08	Crystalline bis[(e)-7-[4-(4-fluorophenyl)-6-isopropyl-2-[methyl(methylsulfonyl)amino]pyrimidin-5-yl](3R,5S)-3,5-dihydroxyhept-6-enoic acid]calcium salt
JPH0524135B2 (de)	1993-04-06
KR20090114398A (ko)	2009-11-03	(ｅ)-2,6-다이알콕시스티릴 4-치환된 벤질설폰의 비경구 투여용 제형
CA2001574A1 (en)	1990-05-11	Pharmaceutical preparation for percutaneous administration containing bunazosin or its salts
GB2217595A (en)	1989-11-01	Anti-inflammatory gel
EP0403578A1 (de)	1990-12-27	Stabile pharmazeutische zusammensetzung.
LV10094B (en)	1995-02-20	Novel pilocarpine derivatives and process for their preparation
CH683427A5 (fr)	1994-03-15	Composé d'isoquinoléine comme agents de blocage neuromusculaire.
EP0440811B1 (de)	1993-11-10	Zubereitung zur perkutanen anwendung
JPH0149704B2 (de)	1989-10-25
EP0106541A2 (de)	1984-04-25	Vor-Arzneimittel von Pilocarpin
US5436350A (en)	1995-07-25	Bispilocarpic acid ester derivatives and process for their preparation
LV10257B (en)	1995-06-20	Novel pilocarpine derivatives and process for their preparation
JP2623580B2 (ja)	1997-06-25	消炎鎮痛クリーム剤
FI98910C (fi)	1997-09-10	Menetelmä farmaseuttisesti käyttökelpoisten pilokarpiinijohdannaisten valmistamiseksi
US4124723A (en)	1978-11-07	Method for suppressing histamine release
CA1148165A (en)	1983-06-14	Esters of arylpropionic acids endowed with an anti- inflammatory activity, process for their preparation, and related pharmaceutical compositions
FI98911C (fi)	1997-09-10	Menetelmä farmaseuttisesti käyttökelpoisten pilokarpiinijohdannaisten valmistamiseksi
EP0220409A2 (de)	1987-05-06	GEM-Dihalo und Tetrahalo-1,12-diamino-4,9-diaza-dodecane
JP3098275B2 (ja)	2000-10-16	トルナフテート含有液剤
RU2803145C2 (ru)	2023-09-07	Кристаллический пиримидинил-3,8-диазабицикло[3.2.1]октанилметанон и его применение
CN106279018A (zh)	2017-01-04	β2-受体兴奋剂及其制备方法和应用
FI109087B (fi)	2002-05-31	Menetelmä farmaseuttisen koostumuksen valmistamiseksi
EP0693481A1 (de)	1996-01-24	Prodrugs von 5,5-Diphenylhydantoin als antiepileptische und antiarrhythmische Mittel