SK8295A3 - N/exp_g/-monomethyl-l-arginine hydrochloride derivatives and their use in the treatment of septic shock - Google Patents

N/exp_g/-monomethyl-l-arginine hydrochloride derivatives and their use in the treatment of septic shock Download PDF

Info

Publication number: SK8295A3
Authority: SK; Slovakia
Prior art keywords: monomethyl; hydrochloride; arginine; salt; argimine
Prior art date: 1992-07-24

Application number

SK82-95A

Other languages

English (en)

Slovak (sk)

Inventor

Harold F Hodson

Original Assignee

Wellcome Found

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.)

1992-07-24

Filing date

1993-07-23

Publication date

1995-07-11

1993-07-23 Application filed by Wellcome Found filed Critical Wellcome Found

1995-07-11 Publication of SK8295A3 publication Critical patent/SK8295A3/sk

Links

206010040070 Septic Shock Diseases 0.000 title claims description 9
230000036303 septic shock Effects 0.000 title claims description 9
238000011282 treatment Methods 0.000 title claims description 9
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 6
239000003814 drug Substances 0.000 claims abstract description 4
238000002360 preparation method Methods 0.000 claims abstract description 4
QYGXVJHXZUSLQC-JEDNCBNOSA-N (2s)-2-amino-5-[(n'-methylcarbamimidoyl)amino]pentanoic acid;hydron;chloride Chemical compound Cl.CN=C(N)NCCC[C@H](N)C(O)=O QYGXVJHXZUSLQC-JEDNCBNOSA-N 0.000 claims abstract 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 38
NTNWOCRCBQPEKQ-YFKPBYRVSA-N N(omega)-methyl-L-arginine Chemical compound CN=C(N)NCCC[C@H](N)C(O)=O NTNWOCRCBQPEKQ-YFKPBYRVSA-N 0.000 claims description 32
NTNWOCRCBQPEKQ-UHFFFAOYSA-N NG-mono-methyl-L-arginine Natural products CN=C(N)NCCCC(N)C(O)=O NTNWOCRCBQPEKQ-UHFFFAOYSA-N 0.000 claims description 30
238000000034 method Methods 0.000 claims description 17
150000003839 salts Chemical class 0.000 claims description 12
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims description 10
230000008569 process Effects 0.000 claims description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
239000013078 crystal Substances 0.000 claims description 6
239000004615 ingredient Substances 0.000 claims description 6
238000011321 prophylaxis Methods 0.000 claims description 6
238000002425 crystallisation Methods 0.000 claims description 5
230000008025 crystallization Effects 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 5
238000010899 nucleation Methods 0.000 claims description 5
239000007787 solid Substances 0.000 claims description 5
229960003589 arginine hydrochloride Drugs 0.000 claims description 3
230000008018 melting Effects 0.000 claims description 3
238000002844 melting Methods 0.000 claims description 3
239000003937 drug carrier Substances 0.000 claims description 2
230000001225 therapeutic effect Effects 0.000 claims description 2
239000000203 mixture Substances 0.000 description 20
239000000243 solution Substances 0.000 description 19
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
239000004480 active ingredient Substances 0.000 description 11
MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 8
150000001875 compounds Chemical class 0.000 description 6
238000009472 formulation Methods 0.000 description 5
239000007788 liquid Substances 0.000 description 5
239000003826 tablet Substances 0.000 description 5
201000010099 disease Diseases 0.000 description 4
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
-1 imino (methylamino) methyl Chemical group 0.000 description 4
239000000126 substance Substances 0.000 description 4
208000001953 Hypotension Diseases 0.000 description 3
AHLPHDHHMVZTML-BYPYZUCNSA-N L-Ornithine Chemical compound NCCC[C@H](N)C(O)=O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 description 3
AHLPHDHHMVZTML-UHFFFAOYSA-N Orn-delta-NH2 Natural products NCCCC(N)C(O)=O AHLPHDHHMVZTML-UHFFFAOYSA-N 0.000 description 3
UTJLXEIPEHZYQJ-UHFFFAOYSA-N Ornithine Natural products OC(=O)C(C)CCCN UTJLXEIPEHZYQJ-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
238000000113 differential scanning calorimetry Methods 0.000 description 3
239000008187 granular material Substances 0.000 description 3
230000036543 hypotension Effects 0.000 description 3
238000002347 injection Methods 0.000 description 3
239000007924 injection Substances 0.000 description 3
229960003104 ornithine Drugs 0.000 description 3
239000000843 powder Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
GGTYBZJRPHEQDG-WCCKRBBISA-N (2s)-2,5-diaminopentanoic acid hydrochloride Chemical compound Cl.NCCC[C@H](N)C(O)=O GGTYBZJRPHEQDG-WCCKRBBISA-N 0.000 description 2
241000220479 Acacia Species 0.000 description 2
239000004475 Arginine Substances 0.000 description 2
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
235000010643 Leucaena leucocephala Nutrition 0.000 description 2
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
229930006000 Sucrose Natural products 0.000 description 2
239000002253 acid Substances 0.000 description 2
229960003121 arginine Drugs 0.000 description 2
ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 2
150000001483 arginine derivatives Chemical class 0.000 description 2
239000002585 base Substances 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
238000009835 boiling Methods 0.000 description 2
239000002775 capsule Substances 0.000 description 2
239000000969 carrier Substances 0.000 description 2
238000004090 dissolution Methods 0.000 description 2
238000001990 intravenous administration Methods 0.000 description 2
239000000463 material Substances 0.000 description 2
238000000465 moulding Methods 0.000 description 2
229960003244 ornithine hydrochloride Drugs 0.000 description 2
229920001467 poly(styrenesulfonates) Polymers 0.000 description 2
239000011347 resin Substances 0.000 description 2
229920005989 resin Polymers 0.000 description 2
239000002904 solvent Substances 0.000 description 2
238000007920 subcutaneous administration Methods 0.000 description 2
239000005720 sucrose Substances 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
238000004809 thin layer chromatography Methods 0.000 description 2
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
241000416162 Astragalus gummifer Species 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
229920001615 Tragacanth Polymers 0.000 description 1
238000002441 X-ray diffraction Methods 0.000 description 1
UDUMWDDMSHXGGQ-UHFFFAOYSA-N [amino(methylsulfanyl)methylidene]-methylazanium;iodide Chemical compound I.CSC(N)=NC UDUMWDDMSHXGGQ-UHFFFAOYSA-N 0.000 description 1
IKPNWIGTWUZCKM-JEDNCBNOSA-N acetic acid;(2s)-2-amino-5-[(n'-methylcarbamimidoyl)amino]pentanoic acid Chemical compound CC(O)=O.CN=C(N)NCCC[C@H](N)C(O)=O IKPNWIGTWUZCKM-JEDNCBNOSA-N 0.000 description 1
PQLVXDKIJBQVDF-UHFFFAOYSA-N acetic acid;hydrate Chemical compound O.CC(O)=O PQLVXDKIJBQVDF-UHFFFAOYSA-N 0.000 description 1
230000009471 action Effects 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
230000003385 bacteriostatic effect Effects 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
239000008280 blood Substances 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
230000037396 body weight Effects 0.000 description 1
239000000872 buffer Substances 0.000 description 1
210000004027 cell Anatomy 0.000 description 1
229940110456 cocoa butter Drugs 0.000 description 1
235000019868 cocoa butter Nutrition 0.000 description 1
239000007891 compressed tablet Substances 0.000 description 1
238000007906 compression Methods 0.000 description 1
230000006835 compression Effects 0.000 description 1
238000013270 controlled release Methods 0.000 description 1
239000012050 conventional carrier Substances 0.000 description 1
229940127089 cytotoxic agent Drugs 0.000 description 1
239000002254 cytotoxic agent Substances 0.000 description 1
231100000599 cytotoxic agent Toxicity 0.000 description 1
230000003013 cytotoxicity Effects 0.000 description 1
231100000135 cytotoxicity Toxicity 0.000 description 1
230000002939 deleterious effect Effects 0.000 description 1
HDRXZJPWHTXQRI-BHDTVMLSSA-N diltiazem hydrochloride Chemical compound [Cl-].C1=CC(OC)=CC=C1[C@H]1[C@@H](OC(C)=O)C(=O)N(CC[NH+](C)C)C2=CC=CC=C2S1 HDRXZJPWHTXQRI-BHDTVMLSSA-N 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
230000002500 effect on skin Effects 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
210000003038 endothelium Anatomy 0.000 description 1
210000003989 endothelium vascular Anatomy 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
235000013355 food flavoring agent Nutrition 0.000 description 1
239000012458 free base Substances 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
235000011187 glycerol Nutrition 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
230000009215 host defense mechanism Effects 0.000 description 1
125000001841 imino group Chemical group [H]N=* 0.000 description 1
230000001939 inductive effect Effects 0.000 description 1
239000003701 inert diluent Substances 0.000 description 1
238000001802 infusion Methods 0.000 description 1
230000000977 initiatory effect Effects 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
239000007937 lozenge Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
210000002540 macrophage Anatomy 0.000 description 1
238000001819 mass spectrum Methods 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
239000007932 molded tablet Substances 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
230000002085 persistent effect Effects 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
238000007493 shaping process Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
238000010183 spectrum analysis Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
230000000451 tissue damage Effects 0.000 description 1
231100000827 tissue damage Toxicity 0.000 description 1
238000011200 topical administration Methods 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
238000001665 trituration Methods 0.000 description 1
238000002255 vaccination Methods 0.000 description 1
230000006442 vascular tone Effects 0.000 description 1
230000024883 vasodilation Effects 0.000 description 1
229940124549 vasodilator Drugs 0.000 description 1
239000003071 vasodilator agent Substances 0.000 description 1
238000012800 visualization Methods 0.000 description 1
239000008215 water for injection Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C279/04—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to acyclic carbon atoms of a carbon skeleton
- C07C279/14—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to acyclic carbon atoms of a carbon skeleton being further substituted by carboxyl groups
- 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
- 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
- A61P9/02—Non-specific cardiovascular stimulants, e.g. drugs for syncope, antihypotensives

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
General Chemical & Material Sciences (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Hydrogenated Pyridines (AREA)
Peptides Or Proteins (AREA)
Medicinal Preparation (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Pyrrole Compounds (AREA)

SK82-95A 1992-07-24 1993-07-23 N/exp_g/-monomethyl-l-arginine hydrochloride derivatives and their use in the treatment of septic shock SK8295A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB929215816A GB9215816D0 (en)	1992-07-24	1992-07-24	Arginine derivatives
PCT/GB1993/001563 WO1994002453A1 (en)	1992-07-24	1993-07-23	Ng-monomethyl-l-arginine hydrochloride derivatives and their use in the treatment of septic shock

Publications (1)

Publication Number	Publication Date
SK8295A3 true SK8295A3 (en)	1995-07-11

Family

ID=10719277

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK82-95A SK8295A3 (en)	1992-07-24	1993-07-23	N/exp_g/-monomethyl-l-arginine hydrochloride derivatives and their use in the treatment of septic shock

Country Status (24)

Country	Link
EP (1)	EP0651741B1 (de)
JP (1)	JP2878844B2 (de)
KR (1)	KR950702528A (de)
CN (1)	CN1087624A (de)
AT (1)	ATE148451T1 (de)
CA (1)	CA2140852A1 (de)
CY (1)	CY2085B1 (de)
CZ (1)	CZ8095A3 (de)
DE (1)	DE69307894T2 (de)
DK (1)	DK0651741T3 (de)
ES (1)	ES2098051T3 (de)
GB (1)	GB9215816D0 (de)
GR (1)	GR3022773T3 (de)
HU (1)	HU210876A9 (de)
IL (1)	IL106463A (de)
MX (1)	MX9304466A (de)
NO (1)	NO302360B1 (de)
NZ (1)	NZ254865A (de)
PL (1)	PL307238A1 (de)
RU (1)	RU95105249A (de)
SG (1)	SG46425A1 (de)
SK (1)	SK8295A3 (de)
WO (1)	WO1994002453A1 (de)
ZA (1)	ZA935348B (de)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5424447A (en) *	1993-07-07	1995-06-13	The Medical College Of Wisconsin Research Foundation, Inc.	Heme binding compounds and use thereof
GB9603522D0 (en) *	1996-02-20	1996-04-17	Wellcome Found	Chemical process
AU2004207720A1 (en) *	2003-01-31	2004-08-12	Teijin Pharma Limited	Crystal of (23S)-1alpha-hydroxy-27-nor-25-methylenevitamin D3-26,23-lactone and process for producing the same
CN1724514B (zh) *	2004-07-19	2010-06-09	上海依福瑞实业有限公司	一种l－高精氨酸盐酸盐的制备方法
US20100158857A1 (en) *	2006-05-23	2010-06-24	University Of Utah Research Foundation	Compositions and methods for the inhibition of endothelial nitric oxide synthase activity

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5028627A (en) *	1989-09-13	1991-07-02	Cornell Research Foundation, Inc.	Method of using arginine derivatives to inhibit systemic hypotension associated with nitric oxide production or endothelial derived relaxing factor

1992
- 1992-07-24 GB GB929215816A patent/GB9215816D0/en active Pending
1993
- 1993-07-23 PL PL93307238A patent/PL307238A1/xx unknown
- 1993-07-23 DE DE69307894T patent/DE69307894T2/de not_active Expired - Fee Related
- 1993-07-23 SK SK82-95A patent/SK8295A3/sk unknown
- 1993-07-23 KR KR1019950700192A patent/KR950702528A/ko not_active Abandoned
- 1993-07-23 CA CA002140852A patent/CA2140852A1/en not_active Abandoned
- 1993-07-23 ES ES93917905T patent/ES2098051T3/es not_active Expired - Lifetime
- 1993-07-23 RU RU95105249/04A patent/RU95105249A/ru unknown
- 1993-07-23 CN CN93109375A patent/CN1087624A/zh active Pending
- 1993-07-23 NZ NZ254865A patent/NZ254865A/en unknown
- 1993-07-23 DK DK93917905.7T patent/DK0651741T3/da active
- 1993-07-23 JP JP6504312A patent/JP2878844B2/ja not_active Expired - Lifetime
- 1993-07-23 WO PCT/GB1993/001563 patent/WO1994002453A1/en not_active Ceased
- 1993-07-23 ZA ZA935348A patent/ZA935348B/xx unknown
- 1993-07-23 MX MX9304466A patent/MX9304466A/es not_active IP Right Cessation
- 1993-07-23 IL IL10646393A patent/IL106463A/en not_active IP Right Cessation
- 1993-07-23 AT AT93917905T patent/ATE148451T1/de not_active IP Right Cessation
- 1993-07-23 EP EP93917905A patent/EP0651741B1/de not_active Expired - Lifetime
- 1993-07-23 CZ CZ9580A patent/CZ8095A3/cs unknown
- 1993-07-23 SG SG1996004597A patent/SG46425A1/en unknown
1995
- 1995-01-23 NO NO950248A patent/NO302360B1/no unknown
- 1995-06-02 HU HU95P/P00152P patent/HU210876A9/hu unknown
1997
- 1997-03-07 GR GR970400457T patent/GR3022773T3/el unknown
1999
- 1999-03-05 CY CY9902085A patent/CY2085B1/xx unknown

Also Published As

Publication number	Publication date
ATE148451T1 (de)	1997-02-15
ZA935348B (en)	1995-01-23
CZ8095A3 (en)	1995-10-18
CY2085B1 (en)	1999-03-05
EP0651741B1 (de)	1997-01-29
KR950702528A (ko)	1995-07-29
HU210876A9 (en)	1995-09-28
NO950248L (no)	1995-01-23
IL106463A (en)	1998-08-16
CA2140852A1 (en)	1994-02-03
DE69307894T2 (de)	1997-06-12
PL307238A1 (en)	1995-05-15
MX9304466A (es)	1994-04-29
CN1087624A (zh)	1994-06-08
AU669557B2 (en)	1996-06-13
NO302360B1 (no)	1998-02-23
DK0651741T3 (da)	1997-05-12
GB9215816D0 (en)	1992-09-09
JP2878844B2 (ja)	1999-04-05
GR3022773T3 (en)	1997-06-30
EP0651741A1 (de)	1995-05-10
AU4715793A (en)	1994-02-14
NO950248D0 (no)	1995-01-23
RU95105249A (ru)	1996-10-27
IL106463A0 (en)	1993-11-15
WO1994002453A1 (en)	1994-02-03
JPH07509239A (ja)	1995-10-12
NZ254865A (en)	1996-10-28
DE69307894D1 (de)	1997-03-13
ES2098051T3 (es)	1997-04-16
SG46425A1 (en)	1998-02-20

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SK8295A3 (en)	1995-07-11	N/exp_g/-monomethyl-l-arginine hydrochloride derivatives and their use in the treatment of septic shock
JPS60174783A (ja)	1985-09-09	新規８α‐アシルアミノエルゴリン類
JP3190679B2 (ja)	2001-07-23	複素環式化学
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