JPS6050789B2 - 気管支分泌促進活性、粘液流動化活性及び咳止め活性を有する新規な化合物、その製法及びそれを含有する製薬組成物 - Google Patents
気管支分泌促進活性、粘液流動化活性及び咳止め活性を有する新規な化合物、その製法及びそれを含有する製薬組成物Info
- Publication number
- JPS6050789B2 JPS6050789B2 JP58142379A JP14237983A JPS6050789B2 JP S6050789 B2 JPS6050789 B2 JP S6050789B2 JP 58142379 A JP58142379 A JP 58142379A JP 14237983 A JP14237983 A JP 14237983A JP S6050789 B2 JPS6050789 B2 JP S6050789B2
- Authority
- JP
- Japan
- Prior art keywords
- activity
- same
- pharmaceutical composition
- thiazolidine
- producing
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired
Links
- 150000001875 compounds Chemical class 0.000 title claims description 11
- 229940124584 antitussives Drugs 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims description 7
- 210000003097 mucus Anatomy 0.000 title claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 4
- 230000000694 effects Effects 0.000 title description 15
- 230000000580 secretagogue effect Effects 0.000 title description 7
- 239000003434 antitussive agent Substances 0.000 title description 6
- LHGVFZTZFXWLCP-UHFFFAOYSA-N pyrocatechol monomethyl ether Natural products COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 claims description 17
- 229960001867 guaiacol Drugs 0.000 claims description 9
- WXTBYSIPOKXCPM-UHFFFAOYSA-N 3-acetyl-1,3-thiazolidine-4-carboxylic acid Chemical compound CC(=O)N1CSCC1C(O)=O WXTBYSIPOKXCPM-UHFFFAOYSA-N 0.000 claims description 6
- 230000000954 anitussive effect Effects 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- DZLNHFMRPBPULJ-UHFFFAOYSA-N thioproline Chemical compound OC(=O)C1CSCN1 DZLNHFMRPBPULJ-UHFFFAOYSA-N 0.000 claims description 3
- 229950001139 timonacic Drugs 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 2
- -1 guaiacol N-acetyl-4-thiazolidine-carboxylate compound Chemical class 0.000 claims description 2
- 230000007935 neutral effect Effects 0.000 claims description 2
- 239000000829 suppository Substances 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 3
- 150000008064 anhydrides Chemical class 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical compound C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 claims 1
- 238000005538 encapsulation Methods 0.000 claims 1
- 238000005243 fluidization Methods 0.000 claims 1
- 230000001737 promoting effect Effects 0.000 claims 1
- 230000028327 secretion Effects 0.000 claims 1
- 235000020357 syrup Nutrition 0.000 claims 1
- 239000006188 syrup Substances 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- OROGSEYTTFOCAN-DNJOTXNNSA-N codeine Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC OROGSEYTTFOCAN-DNJOTXNNSA-N 0.000 description 6
- DZLNHFMRPBPULJ-VKHMYHEASA-N L-thioproline Chemical compound OC(=O)[C@@H]1CSCN1 DZLNHFMRPBPULJ-VKHMYHEASA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 241000283973 Oryctolagus cuniculus Species 0.000 description 3
- 229960004126 codeine Drugs 0.000 description 3
- OROGSEYTTFOCAN-UHFFFAOYSA-N hydrocodone Natural products C1C(N(CCC234)C)C2C=CC(O)C3OC2=C4C1=CC=C2OC OROGSEYTTFOCAN-UHFFFAOYSA-N 0.000 description 3
- 230000003285 pharmacodynamic effect Effects 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
- 239000012346 acetyl chloride Substances 0.000 description 2
- 230000007059 acute toxicity Effects 0.000 description 2
- 231100000403 acute toxicity Toxicity 0.000 description 2
- 239000000443 aerosol Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 210000004072 lung Anatomy 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- JJVXHDTWVIPRBZ-VKHMYHEASA-N (2r)-2-[carboxy(methyl)amino]-3-sulfanylpropanoic acid Chemical compound OC(=O)N(C)[C@@H](CS)C(O)=O JJVXHDTWVIPRBZ-VKHMYHEASA-N 0.000 description 1
- OMNGOGILVBLKAS-UHFFFAOYSA-N 2-methoxyphenol Chemical compound COC1=CC=CC=C1O.COC1=CC=CC=C1O OMNGOGILVBLKAS-UHFFFAOYSA-N 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- 241000272201 Columbiformes Species 0.000 description 1
- 206010011224 Cough Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 1
- YTGJWQPHMWSCST-UHFFFAOYSA-N Tiopronin Chemical compound CC(S)C(=O)NCC(O)=O YTGJWQPHMWSCST-UHFFFAOYSA-N 0.000 description 1
- 108010058907 Tiopronin Proteins 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000001086 cytosolic effect Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 230000001483 mobilizing effect Effects 0.000 description 1
- 230000000510 mucolytic effect Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- ULSZVNJBVJWEJE-UHFFFAOYSA-N thiazolidine-2-carboxylic acid Chemical class OC(=O)C1NCCS1 ULSZVNJBVJWEJE-UHFFFAOYSA-N 0.000 description 1
- 229960004402 tiopronin Drugs 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 230000010415 tropism Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/04—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D277/06—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/10—Expectorants
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pulmonology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT22764/82A IT1190945B (it) | 1982-08-06 | 1982-08-06 | Composto ad azione broncosegretogoga,fluidificante ed antitussigena,procedimento per la sua preparazione e composizioni farmaceutiche che lo contengono |
| IT22764-A/82 | 1982-08-06 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5944367A JPS5944367A (ja) | 1984-03-12 |
| JPS6050789B2 true JPS6050789B2 (ja) | 1985-11-11 |
Family
ID=11200186
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58142379A Expired JPS6050789B2 (ja) | 1982-08-06 | 1983-08-03 | 気管支分泌促進活性、粘液流動化活性及び咳止め活性を有する新規な化合物、その製法及びそれを含有する製薬組成物 |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JPS6050789B2 (enrdf_load_stackoverflow) |
| DE (1) | DE3325677A1 (enrdf_load_stackoverflow) |
| ES (1) | ES524727A0 (enrdf_load_stackoverflow) |
| IT (1) | IT1190945B (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63168794U (enrdf_load_stackoverflow) * | 1987-04-21 | 1988-11-02 |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE74354T1 (de) * | 1988-06-29 | 1992-04-15 | Yason Srl | N-karbethoxy-4-thiazolin-karbonsaeure, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel. |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR8266M (enrdf_load_stackoverflow) * | 1968-12-31 | 1970-10-26 | ||
| FR2222087B1 (enrdf_load_stackoverflow) * | 1973-03-22 | 1976-04-09 | Ferlux |
-
1982
- 1982-08-06 IT IT22764/82A patent/IT1190945B/it active
-
1983
- 1983-07-15 DE DE19833325677 patent/DE3325677A1/de active Granted
- 1983-08-03 JP JP58142379A patent/JPS6050789B2/ja not_active Expired
- 1983-08-04 ES ES524727A patent/ES524727A0/es active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63168794U (enrdf_load_stackoverflow) * | 1987-04-21 | 1988-11-02 |
Also Published As
| Publication number | Publication date |
|---|---|
| ES8502429A1 (es) | 1985-01-01 |
| DE3325677A1 (de) | 1984-02-09 |
| IT8222764A0 (it) | 1982-08-06 |
| JPS5944367A (ja) | 1984-03-12 |
| IT1190945B (it) | 1988-02-24 |
| DE3325677C2 (enrdf_load_stackoverflow) | 1988-04-07 |
| ES524727A0 (es) | 1985-01-01 |
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