ZA200410123B - Annelated pyrrole compounds as proton pump inhibitors for treating ulcer - Google Patents

Annelated pyrrole compounds as proton pump inhibitors for treating ulcer Download PDF

Info

Publication number: ZA200410123B
Authority: ZA; South Africa
Prior art keywords: acid; gastric; alkyl; formula; use according
Prior art date: 2002-05-17

Application number

ZA200410123A

Other languages

English (en)

Inventor

Adam J Smolka

Charles E Hammond

Sandeep Gupta

Original Assignee

Merckle Gmbh

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.)

2002-05-17

Filing date

2004-12-15

Publication date

2006-07-26

2004-12-15 Application filed by Merckle Gmbh filed Critical Merckle Gmbh

2006-07-26 Publication of ZA200410123B publication Critical patent/ZA200410123B/en

Links

208000025865 Ulcer Diseases 0.000 title claims description 12
229940126409 proton pump inhibitor Drugs 0.000 title description 10
239000000612 proton pump inhibitor Substances 0.000 title description 10
150000003233 pyrroles Chemical class 0.000 title description 5
231100000397 ulcer Toxicity 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims description 83
230000002496 gastric effect Effects 0.000 claims description 59
-1 -CHO Chemical group 0.000 claims description 54
125000000217 alkyl group Chemical group 0.000 claims description 42
241000124008 Mammalia Species 0.000 claims description 35
150000003254 radicals Chemical class 0.000 claims description 33
230000002401 inhibitory effect Effects 0.000 claims description 27
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 23
125000003545 alkoxy group Chemical group 0.000 claims description 22
125000003118 aryl group Chemical group 0.000 claims description 19
210000004211 gastric acid Anatomy 0.000 claims description 17
229910052736 halogen Inorganic materials 0.000 claims description 16
150000002367 halogens Chemical class 0.000 claims description 16
125000001424 substituent group Chemical group 0.000 claims description 16
125000001188 haloalkyl group Chemical group 0.000 claims description 15
CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 claims description 14
239000000203 mixture Substances 0.000 claims description 14
239000000041 non-steroidal anti-inflammatory agent Substances 0.000 claims description 14
229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 claims description 14
239000008194 pharmaceutical composition Substances 0.000 claims description 14
108010083204 Proton Pumps Proteins 0.000 claims description 13
125000000753 cycloalkyl group Chemical group 0.000 claims description 13
230000006378 damage Effects 0.000 claims description 13
150000003839 salts Chemical class 0.000 claims description 12
BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 claims description 11
229960001138 acetylsalicylic acid Drugs 0.000 claims description 11
229940121363 anti-inflammatory agent Drugs 0.000 claims description 11
239000002260 anti-inflammatory agent Substances 0.000 claims description 11
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
230000002178 gastroprotective effect Effects 0.000 claims description 11
125000004438 haloalkoxy group Chemical group 0.000 claims description 11
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 11
108091006112 ATPases Proteins 0.000 claims description 10
102000057290 Adenosine Triphosphatases Human genes 0.000 claims description 10
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 10
239000003112 inhibitor Substances 0.000 claims description 10
230000001562 ulcerogenic effect Effects 0.000 claims description 10
125000005422 alkyl sulfonamido group Chemical group 0.000 claims description 9
125000004414 alkyl thio group Chemical group 0.000 claims description 9
125000004429 atom Chemical group 0.000 claims description 9
125000000623 heterocyclic group Chemical group 0.000 claims description 9
230000036269 ulceration Effects 0.000 claims description 9
208000027418 Wounds and injury Diseases 0.000 claims description 8
125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 8
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 8
125000002947 alkylene group Chemical group 0.000 claims description 8
125000004104 aryloxy group Chemical group 0.000 claims description 8
125000004432 carbon atom Chemical group C* 0.000 claims description 8
210000001156 gastric mucosa Anatomy 0.000 claims description 8
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125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
229910052717 sulfur Inorganic materials 0.000 claims description 8
CMWTZPSULFXXJA-UHFFFAOYSA-N Naproxen Natural products C1=C(C(C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-UHFFFAOYSA-N 0.000 claims description 7
229910052739 hydrogen Inorganic materials 0.000 claims description 7
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CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical compound C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 claims description 7
238000002560 therapeutic procedure Methods 0.000 claims description 7
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239000013543 active substance Substances 0.000 claims description 6
CNBGNNVCVSKAQZ-UHFFFAOYSA-N benzydamine Chemical compound C12=CC=CC=C2C(OCCCN(C)C)=NN1CC1=CC=CC=C1 CNBGNNVCVSKAQZ-UHFFFAOYSA-N 0.000 claims description 6
125000002619 bicyclic group Chemical group 0.000 claims description 6
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125000005842 heteroatom Chemical group 0.000 claims description 6
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125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
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QYSPLQLAKJAUJT-UHFFFAOYSA-N piroxicam Chemical compound OC=1C2=CC=CC=C2S(=O)(=O)N(C)C=1C(=O)NC1=CC=CC=N1 QYSPLQLAKJAUJT-UHFFFAOYSA-N 0.000 claims description 6
YREYEVIYCVEVJK-UHFFFAOYSA-N rabeprazole Chemical compound COCCCOC1=CC=NC(CS(=O)C=2NC3=CC=CC=C3N=2)=C1C YREYEVIYCVEVJK-UHFFFAOYSA-N 0.000 claims description 6
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QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 5
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125000004423 acyloxy group Chemical group 0.000 claims description 4
125000004450 alkenylene group Chemical group 0.000 claims description 4
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RDJGLLICXDHJDY-NSHDSACASA-N (2s)-2-(3-phenoxyphenyl)propanoic acid Chemical compound OC(=O)[C@@H](C)C1=CC=CC(OC=2C=CC=CC=2)=C1 RDJGLLICXDHJDY-NSHDSACASA-N 0.000 claims description 3
GUHPRPJDBZHYCJ-SECBINFHSA-N (2s)-2-(5-benzoylthiophen-2-yl)propanoic acid Chemical compound S1C([C@H](C(O)=O)C)=CC=C1C(=O)C1=CC=CC=C1 GUHPRPJDBZHYCJ-SECBINFHSA-N 0.000 claims description 3
MDKGKXOCJGEUJW-VIFPVBQESA-N (2s)-2-[4-(thiophene-2-carbonyl)phenyl]propanoic acid Chemical compound C1=CC([C@@H](C(O)=O)C)=CC=C1C(=O)C1=CC=CS1 MDKGKXOCJGEUJW-VIFPVBQESA-N 0.000 claims description 3
ZHXUEUKVDMWSKV-UHFFFAOYSA-N 1-(3,5-ditert-butyl-4-hydroxyphenyl)hex-5-yn-1-one Chemical compound CC(C)(C)C1=CC(C(=O)CCCC#C)=CC(C(C)(C)C)=C1O ZHXUEUKVDMWSKV-UHFFFAOYSA-N 0.000 claims description 3
JIEKMACRVQTPRC-UHFFFAOYSA-N 2-[4-(4-chlorophenyl)-2-phenyl-5-thiazolyl]acetic acid Chemical compound OC(=O)CC=1SC(C=2C=CC=CC=2)=NC=1C1=CC=C(Cl)C=C1 JIEKMACRVQTPRC-UHFFFAOYSA-N 0.000 claims description 3
SQVNITZYWXMWOG-UHFFFAOYSA-N 2-cyclohexyl-1-(2-methylquinolin-4-yl)-3-(1,3-thiazol-2-yl)guanidine Chemical compound C=12C=CC=CC2=NC(C)=CC=1NC(=NC1CCCCC1)NC1=NC=CS1 SQVNITZYWXMWOG-UHFFFAOYSA-N 0.000 claims description 3
YTRMTPPVNRALON-UHFFFAOYSA-N 2-phenyl-4-quinolinecarboxylic acid Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=CC=C1 YTRMTPPVNRALON-UHFFFAOYSA-N 0.000 claims description 3
FFKUDWZICMJVPA-UHFFFAOYSA-N 2-phosphonooxybenzoic acid Chemical compound OC(=O)C1=CC=CC=C1OP(O)(O)=O FFKUDWZICMJVPA-UHFFFAOYSA-N 0.000 claims description 3
SYCHUQUJURZQMO-UHFFFAOYSA-N 4-hydroxy-2-methyl-1,1-dioxo-n-(1,3-thiazol-2-yl)-1$l^{6},2-benzothiazine-3-carboxamide Chemical compound OC=1C2=CC=CC=C2S(=O)(=O)N(C)C=1C(=O)NC1=NC=CS1 SYCHUQUJURZQMO-UHFFFAOYSA-N 0.000 claims description 3
PJJGZPJJTHBVMX-UHFFFAOYSA-N 5,7-Dihydroxyisoflavone Chemical compound C=1C(O)=CC(O)=C(C2=O)C=1OC=C2C1=CC=CC=C1 PJJGZPJJTHBVMX-UHFFFAOYSA-N 0.000 claims description 3
DVEQCIBLXRSYPH-UHFFFAOYSA-N 5-butyl-1-cyclohexylbarbituric acid Chemical compound O=C1C(CCCC)C(=O)NC(=O)N1C1CCCCC1 DVEQCIBLXRSYPH-UHFFFAOYSA-N 0.000 claims description 3
RLFWWDJHLFCNIJ-UHFFFAOYSA-N Aminoantipyrine Natural products CN1C(C)=C(N)C(=O)N1C1=CC=CC=C1 RLFWWDJHLFCNIJ-UHFFFAOYSA-N 0.000 claims description 3
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RHAXSHUQNIEUEY-UHFFFAOYSA-N Epirizole Chemical compound COC1=CC(C)=NN1C1=NC(C)=CC(OC)=N1 RHAXSHUQNIEUEY-UHFFFAOYSA-N 0.000 claims description 3
RBBWCVQDXDFISW-UHFFFAOYSA-N Feprazone Chemical compound O=C1C(CC=C(C)C)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 RBBWCVQDXDFISW-UHFFFAOYSA-N 0.000 claims description 3
SBDNJUWAMKYJOX-UHFFFAOYSA-N Meclofenamic Acid Chemical compound CC1=CC=C(Cl)C(NC=2C(=CC=CC=2)C(O)=O)=C1Cl SBDNJUWAMKYJOX-UHFFFAOYSA-N 0.000 claims description 3
JZFPYUNJRRFVQU-UHFFFAOYSA-N Niflumic acid Chemical compound OC(=O)C1=CC=CN=C1NC1=CC=CC(C(F)(F)F)=C1 JZFPYUNJRRFVQU-UHFFFAOYSA-N 0.000 claims description 3
ABBQHOQBGMUPJH-UHFFFAOYSA-M Sodium salicylate Chemical compound [Na+].OC1=CC=CC=C1C([O-])=O ABBQHOQBGMUPJH-UHFFFAOYSA-M 0.000 claims description 3
VEQOALNAAJBPNY-UHFFFAOYSA-N antipyrine Chemical compound CN1C(C)=CC(=O)N1C1=CC=CC=C1 VEQOALNAAJBPNY-UHFFFAOYSA-N 0.000 claims description 3
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WOIIIUDZSOLAIW-NSHDSACASA-N azapropazone Chemical compound C1=C(C)C=C2N3C(=O)[C@H](CC=C)C(=O)N3C(N(C)C)=NC2=C1 WOIIIUDZSOLAIW-NSHDSACASA-N 0.000 claims description 3
229960004277 benorilate Drugs 0.000 claims description 3
FEJKLNWAOXSSNR-UHFFFAOYSA-N benorilate Chemical compound C1=CC(NC(=O)C)=CC=C1OC(=O)C1=CC=CC=C1OC(C)=O FEJKLNWAOXSSNR-UHFFFAOYSA-N 0.000 claims description 3
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IVUMCTKHWDRRMH-UHFFFAOYSA-N carprofen Chemical compound C1=CC(Cl)=C[C]2C3=CC=C(C(C(O)=O)C)C=C3N=C21 IVUMCTKHWDRRMH-UHFFFAOYSA-N 0.000 claims description 3
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ZPAKPRAICRBAOD-UHFFFAOYSA-N fenbufen Chemical compound C1=CC(C(=O)CCC(=O)O)=CC=C1C1=CC=CC=C1 ZPAKPRAICRBAOD-UHFFFAOYSA-N 0.000 claims description 3
IDKAXRLETRCXKS-UHFFFAOYSA-N fenclofenac Chemical compound OC(=O)CC1=CC=CC=C1OC1=CC=C(Cl)C=C1Cl IDKAXRLETRCXKS-UHFFFAOYSA-N 0.000 claims description 3
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LPEPZBJOKDYZAD-UHFFFAOYSA-N flufenamic acid Chemical compound OC(=O)C1=CC=CC=C1NC1=CC=CC(C(F)(F)F)=C1 LPEPZBJOKDYZAD-UHFFFAOYSA-N 0.000 claims description 3
OPYFPDBMMYUPME-UHFFFAOYSA-N flumizole Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(OC)=CC=2)NC(C(F)(F)F)=N1 OPYFPDBMMYUPME-UHFFFAOYSA-N 0.000 claims description 3
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IWVCMVBTMGNXQD-UHFFFAOYSA-N terramycin dehydrate Natural products C1=CC=C2C(O)(C)C3C(O)C4C(N(C)C)C(O)=C(C(N)=O)C(=O)C4(O)C(O)=C3C(=O)C2=C1O IWVCMVBTMGNXQD-UHFFFAOYSA-N 0.000 description 1
229960002180 tetracycline Drugs 0.000 description 1
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229940040944 tetracyclines Drugs 0.000 description 1
125000001113 thiadiazolyl group Chemical group 0.000 description 1
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OTVAEFIXJLOWRX-NXEZZACHSA-N thiamphenicol Chemical compound CS(=O)(=O)C1=CC=C([C@@H](O)[C@@H](CO)NC(=O)C(Cl)Cl)C=C1 OTVAEFIXJLOWRX-NXEZZACHSA-N 0.000 description 1
RZWIIPASKMUIAC-VQTJNVASSA-N thromboxane Chemical compound CCCCCCCC[C@H]1OCCC[C@@H]1CCCCCCC RZWIIPASKMUIAC-VQTJNVASSA-N 0.000 description 1
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NLVFBUXFDBBNBW-PBSUHMDJSA-N tobramycin Chemical compound N[C@@H]1C[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N NLVFBUXFDBBNBW-PBSUHMDJSA-N 0.000 description 1
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MYPYJXKWCTUITO-UHFFFAOYSA-N vancomycin Natural products O1C(C(=C2)Cl)=CC=C2C(O)C(C(NC(C2=CC(O)=CC(O)=C2C=2C(O)=CC=C3C=2)C(O)=O)=O)NC(=O)C3NC(=O)C2NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(CC(C)C)NC)C(O)C(C=C3Cl)=CC=C3OC3=CC2=CC1=C3OC1OC(CO)C(O)C(O)C1OC1CC(C)(N)C(O)C(C)O1 MYPYJXKWCTUITO-UHFFFAOYSA-N 0.000 description 1
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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
- A61K31/40—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
- A61K31/403—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 condensed with carbocyclic rings, e.g. carbazole
- 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
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
- 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
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/538—1,4-Oxazines, e.g. morpholine ortho- or peri-condensed with carbocyclic ring systems
- 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
- A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
- A61K31/5415—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame ortho- or peri-condensed with carbocyclic ring systems, e.g. phenothiazine, chlorpromazine, piroxicam
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

Landscapes

Health & Medical Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Veterinary Medicine (AREA)
Chemical & Material Sciences (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Life Sciences & Earth Sciences (AREA)
Epidemiology (AREA)
Organic Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Steroid Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

ZA200410123A 2002-05-17 2004-12-15 Annelated pyrrole compounds as proton pump inhibitors for treating ulcer ZA200410123B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
EP02011081		2002-05-17

Publications (1)

Publication Number	Publication Date
ZA200410123B true ZA200410123B (en)	2006-07-26

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ID=37725454

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
ZA200410123A ZA200410123B (en)	2002-05-17	2004-12-15	Annelated pyrrole compounds as proton pump inhibitors for treating ulcer

Country Status (15)

Country	Link
EP (1)	EP1505964B1 (pt)
JP (1)	JP2006509720A (pt)
CN (1)	CN1309383C (pt)
AU (1)	AU2003232788B2 (pt)
BR (1)	BR0310068A (pt)
CA (1)	CA2484238A1 (pt)
DE (1)	DE60317661T2 (pt)
ES (1)	ES2297204T3 (pt)
MX (1)	MXPA04011097A (pt)
NZ (1)	NZ536444A (pt)
PT (1)	PT1505964E (pt)
RU (1)	RU2336872C2 (pt)
UA (1)	UA77812C2 (pt)
WO (1)	WO2003097041A1 (pt)
ZA (1)	ZA200410123B (pt)

Families Citing this family (6)

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Publication number	Priority date	Publication date	Assignee	Title
DE10351035A1 (de) *	2003-10-31	2005-05-25	Merckle Gmbh Chemisch Pharmazeutische Fabrik	Pharmazeutische Licofelone-Formulierung
PE20070540A1 (es) *	2005-08-30	2007-06-26	Takeda Pharmaceutical	Derivados de pirrol como inhibidores de la secrecion acida
WO2007072503A2 (en) *	2005-12-21	2007-06-28	Panacea Biotec Ltd.	Combinations for managing inflammation and associated disorders
ES2534772T3 (es)	2008-10-31	2015-04-28	C-A-I-R Biosciences Gmbh	Sal de colina y trometamina de licofelona
CN104447490B (zh) *	2014-11-19	2017-06-06	连云港恒运医药有限公司	一种质子泵抑制剂的晶型、制备中间体及其合成方法和医药用途
CN113549079A (zh)	2018-05-25	2021-10-26	正大天晴药业集团股份有限公司	2,3-二氢-1h-吡咯嗪-7-甲酰胺类衍生物及其应用

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DE4419246A1 (de) *	1994-06-01	1995-12-07	Merckle Gmbh	Heteroarylsubstituierte Pyrrolizinverbindungen und deren Anwendung in der Pharmazie
DE4419247A1 (de) *	1994-06-01	1995-12-07	Merckle Gmbh	Sulfonylierte Pyrrolizincarbonsäureamide und deren Anwendung in der Pharmazie
SE9500478D0 (sv) *	1995-02-09	1995-02-09	Astra Ab	New pharmaceutical formulation and process
ES2247604T3 (es) *	1995-06-12	2006-03-01	G.D. SEARLE & CO.	Composiciones que comprenden un inhibidor de ciclooxigenasa-2 y un inhibidor de 5-lipoxigenasa.
US5852033A (en) *	1995-06-29	1998-12-22	Pharma Mar, S.A.	Methods of treatment using lamellarin-class alkaloids
KR100447918B1 (ko) *	1996-07-25	2005-09-28	동아제약주식회사	대장을포함한위장관보호작용을갖는플라본및플라바논화합물
HUP0204336A3 (en) *	1999-11-23	2006-01-30	Merckle Gmbh	Anti-inflammatory oxo derivatives and hydroxy derivatives of pyrrolizines, and their pharmaceutical use and pharmaceutical compositions containing them their
EP1142889A1 (en) *	2000-04-03	2001-10-10	Pfizer Products Inc.	Pyrazole derivatives as anti-inflammatory/analgesic agents

2003
- 2003-05-16 PT PT03752754T patent/PT1505964E/pt unknown
- 2003-05-16 BR BR0310068-5A patent/BR0310068A/pt not_active IP Right Cessation
- 2003-05-16 NZ NZ536444A patent/NZ536444A/en unknown
- 2003-05-16 EP EP03752754A patent/EP1505964B1/en not_active Expired - Lifetime
- 2003-05-16 DE DE60317661T patent/DE60317661T2/de not_active Expired - Fee Related
- 2003-05-16 CN CNB038112469A patent/CN1309383C/zh not_active Expired - Fee Related
- 2003-05-16 RU RU2004136994/15A patent/RU2336872C2/ru not_active IP Right Cessation
- 2003-05-16 WO PCT/EP2003/005171 patent/WO2003097041A1/en not_active Ceased
- 2003-05-16 UA UA20041210349A patent/UA77812C2/uk unknown
- 2003-05-16 CA CA002484238A patent/CA2484238A1/en not_active Abandoned
- 2003-05-16 MX MXPA04011097A patent/MXPA04011097A/es active IP Right Grant
- 2003-05-16 AU AU2003232788A patent/AU2003232788B2/en not_active Ceased
- 2003-05-16 JP JP2004505040A patent/JP2006509720A/ja active Pending
- 2003-05-16 ES ES03752754T patent/ES2297204T3/es not_active Expired - Lifetime
2004
- 2004-12-15 ZA ZA200410123A patent/ZA200410123B/en unknown

Also Published As

Publication number	Publication date
AU2003232788A1 (en)	2003-12-02
JP2006509720A (ja)	2006-03-23
ES2297204T3 (es)	2008-05-01
DE60317661T2 (de)	2008-10-30
RU2336872C2 (ru)	2008-10-27
PT1505964E (pt)	2008-02-28
CA2484238A1 (en)	2003-11-27
WO2003097041A1 (en)	2003-11-27
AU2003232788B2 (en)	2008-10-02
EP1505964A1 (en)	2005-02-16
CN1309383C (zh)	2007-04-11
NZ536444A (en)	2006-12-22
UA77812C2 (en)	2007-01-15
RU2004136994A (ru)	2005-06-10
MXPA04011097A (es)	2005-02-14
CN1652771A (zh)	2005-08-10
EP1505964B1 (en)	2007-11-21
BR0310068A (pt)	2005-03-08
DE60317661D1 (de)	2008-01-03

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Sachs et al.	2010	Novel approaches to inhibition of gastric acid secretion
RU2252032C2 (ru)	2005-05-20	Новое применение соединений в качестве антибактериальных средств
DE69936150T2 (de)	2008-01-31	Indomethacin-amidderivate zur antiangiogenen und/oder antitumorigen verwendung
Lanas et al.	2003	Clinical implications of COX-1 and/or COX-2 inhibition for the distal gastrointestinal tract
RU2009131454A (ru)	2011-02-27	Способы предупреждения или уменьшения числа обострений подагры с применением ингибиторов ксантиноксидоредуктазы и противовоспалительных средств
ES2996895T3 (en)	2025-02-13	Pharmaceutical composition comprising antiplatelet agent and gastric acid secretion inhibitor
Dajani et al.	2000	Novel therapeutic approaches to gastric and duodenal ulcers: an update
JP2003521516A (ja)	2003-07-15	胃運動刺激剤としてのｃｏｘ−２阻害剤の使用
US20060040945A1 (en)	2006-02-23	Annellated pyrrole compounds as proton pump inhibitors for treating ulcer
La Corte et al.	1999	Prophylaxis and treatment of NSAID-induced gastroduodenal disorders
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AU2003232788B2 (en)	2008-10-02	Annelated pyrrole compounds as proton pump inhibitors for treating ulcer
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ULC	2018	Esomeprazole Magnesium Delayed Release Tablets 20 and 40 mg esomeprazole (as esomeprazole magnesium)
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